Extra! Extra! Read All About It!
by OtakuGirl11324
Summary: Dean is living a normal life as something he never thought he would be, A teacher. Castiel is an actor that just wants someone to love him for him. Dean's life is boring, and he glides by doing mundane everyday things. Castiel's life is hectic and he has been stripped of privacy. And what happens because of a brother's quarrel is enough to alter both of their lives forever.
1. Chapter 1: Because of A Quarrel

Hey guys! This is my first fic for Supernatural, so I apologize if the characters are a bit ooc, but I tried my best. Also this isn't beta'd so there is definitely going to be some mistakes, so if you see any then feel free to tell me if you want xD

As for updates, I am posting this as I write it, so if you like it, tell me and I will try my hardest to get a chapter up weekly (but I'm a college student so I apologize in advance)

ALSO! I made this story to be posted on archive of our own because I wanted to add pictures, and because I don't think I can add pictures on here I am HIGHLY suggesting you read this on AO3, but if you don't want to or can't then it's fine, there just won't be pictures and I will try to add the captions I have in the pictures. It will look like this:

{picture of (whatever the picture is of)}

Caption: (whatever is in the picture's caption)

That's all I have to say, I hope you like it!

* * *

 **Chapter 1: Because of A Quarrel**

"I would have known that." A girl with brown hair says looking at a boy across her table.

The boy rolls his eyes and leans back in his chair, arms crossing over his chest. "Yeah, I'm sure you would have."

"I would have!" She nearly yells slamming a palm on her desk's top. "I know everything about Castiel." She smirks and settles back looking rather confident. "Quiz me right now if you don't believe me."

"Oh, no I believe you. You're stalker worthy material all right." The boy chides with a shit eating grin.

She gasps, thoroughly offended, "Take that back."

"Why should I? You stalk him. You just admit you know everything about him, and he doesn't even know you exist." He shrugs, "You're a stalker."

Her mouth opens to protest, but when nothing comes out she closes it again. The expression on her face resembling that of a wounded puppy. Her voice is quiet when she says, "I didn't… I just really admire him. I didn't…"

Seeing this has gone on long enough, and that the boy now crushed her for admiring her idol, Dean takes that moment to step in to stop his students. "Okay, that's enough, Carlos. Don't throw that word out there like that. It is perfectly fine to want to know as much as you can about those you respect. It isn't stalking if she knows everything he has talked about openly to the world. That just makes her dedicated. A stalker is someone who harasses the person in an often illegal or threatening way."

Carlos drops his eyes from Dean's piercing stare to his hands, unable to hold his stare any longer. "Sorry."

Dean sighs rubbing the back of his neck. These kids. "Just make sure you know the definition of a word before you throw it out in a conversation to insult someone. Actually, scratch that, don't insult people. Now get back to work, I should yell at you for getting off topic."

Carlos apologizes again and buries his nose back into his work laying atop his desk, trying not to think about just getting yelled at in front of the entire class. Dean's eyes slide over to Ann who is thinning her lips, he gives her a small smile then goes back to grading some papers.

He questions every day he steps into this building how exactly he became a teacher. God, he hated teachers when he was in school, and swore to himself that once he graduated school he would never step foot in another one. Honestly he wanted to be a mechanic seeing cars are is passion, but life doesn't always go the way anyone expects it. So yeah, he never expected to be the thing he hated so much.

But now that he's a teacher, he sees the other side to things that he refused to see when he was in school. The students, oh man, they're worse than the devil sometimes. They have absolutely no filter whatsoever, and try making everyone feel like shit just to make themselves feel better. Little assholes are what they are, but Dean isn't allowed to call them that if he wants to keep his job, so if anyone asks, his answer is that they are temperamental teens. Dean now sees why all his teachers hated him with such a passion before and doesn't blame them for their acrimony.

There is always that one kid in each class. That one who bequeathed Dean's shitty attitude and gives either the teachers or students hell. In this class it's Carlos. Carlos is always looking for something to tease someone about. How the debate started today was simple. Ann was talking to her friend about Castiel, the actor who plays Misha on the show Mishapocalypse, that's when Carlos butted his nose into a conversation that had nothing to do with him … again.

But Dean tries to take his brother's advice and look on the bright side of things with this job. He gets to be the one to help these kids become better adults, and that is always enough to make Dean smile and it's worth all the aggravation. Even if it doesn't feel like it in the moment, like right now he feels like it's hopeless for Carlos seeing he hasn't changed at all over the years.

The only thing crossing his mind is _'It's only Tuesday…'_

A faint smile appears on Dean's lips at that thought after a disgruntled moment. It's Tuesday, meaning, Mishapocalypse is on tonight. Also meaning takeout, junk food, and relaxing in pajamas watching the new episode with his little brother.

Tuesdays are great.

When Sam had told Dean about the show, he wasn't necessarily interested. It sounded odd and he honestly wasn't sure how Sam enjoyed it so much, but Dean will admit his quick judgment. Misha, the main character, is given so much life by Castiel that Dean was enraptured the moment he came on the screen, looked around, and flashed that big grin of his. If Dean were being honest with himself he would say his heart fluttered a bit in that moment seeing the intensity in those striking blue eyes, but he plays it off as if it was a completely normal thing, and not as if he had just formed the biggest crush on a man he had ever had.

Although that's another thing. He doesn't crush on people, especially not on men, or at least that's what he has been telling himself as to not disappoint his father or anyone else in his life. And even if deep down he knows what the feelings are, he won't ever admit them to himself.

So the immediate reaction his heart had to Castiel was a shock to Dean, and from that moment till the end of the episode he acted as if the show wasn't anything special. It was simply 'okay', but in honesty, whether it was because of Castiel or the fact the show was actually amazing, he rather enjoyed the first episode and knew he'd enjoy binging the seasons beforehand.

Of course, Sam had found him binging the episodes, but wisely kept his mouth shut about him actually liking it, and instead just decided to sit next to him on the couch to watch along. In which Dean was, and still is, very grateful to his brother for not making a big deal about his liking for the show because Dean really didn't want to have to give up watching it out of petulance to show Sam he really didn't like it.

But that was years ago now and Dean has admit to loving the show on multiple occasions, but of course Sam already knew this, and Dean was yet again thankful to his brother for playing innocent.

The bell rings indicating the end of class and he looks up surprised. Had he really been spacing out that long?

He has to quickly say, "Have a good day, stay out of trouble." to all the students before they stampede out the door. The students all gather their things and practically run to the door, most of them not pushing their chairs in as they leave for the end of the day. Dean sighs and rubs his face, just sitting there for a few moments after he is finally alone.

Deciding it would be much more comfortable to grade the rest of these papers in the comfort of his own home rather than at a hard desk, he gathers the papers and stuffs them into his bag and slings it over his shoulder. He was supposed to finish grading these dang things before the end of the day, but it turns out old habits die hard, daydreaming is one impossible habit to break.

As he walks out his classroom, he runs over the options for dinner. There are quite a few, but not all of them deliver, and he won't feel like running back out seeing Mishapocalypse will be on. Pulling out his phone he is about to dial his brother's number to see what he wants for dinner when someone calls his name from behind him. He turns around seeing Charlie walking towards him with a smile.

"Charlie," Dean gives her a smile. "What brings you here?"

"Oh you know," She shrugs, "I get paid to be here and put up with hormonal teens."

"Well isn't that a coincidence, so do I."

A small warm smile escapes her, and when it dies down she gives him a fond look. "I have to know, I heard some kids teasing Carlos about getting his ass chewed on by you. What happened?"

Dean lets out an exasperated sigh and an over dramatic eyeroll. "That kid never learns, does he?" Dean crosses his arms over his chest with a shake of his head. "He was making fun of Ann and he called her a stalker for admiring Castiel and knowing a lot about him, so I told him to chill out. Stalker is a harsh word and it looked like he hurt her feelings." He shrugs as if he didn't take any of what Carlos said personally. "I didn't really raise my voice, just laid it out there that it wasn't appreciated or nice to say those things."

Charlie has a sly smirk spread across her lips as if she can see through him like glass. "Is that so?"

Dean narrows his eyes not liking that smirk. "I know what you're thinking, Charlie, so stop it now."

"Oh, but Dean, I have no idea what you're talking about."

"Yeah, sure." He scoffs pulling his phone back up and pulling up Sam's number. "You're a wolf in sheep's clothing, Charlie."

"Aw, thank you Dean." She puts a hand on his arm and walks past him with a wink. "Have fun watching Mishapocalypse tonight."

"I will." Dean smirks, "Have fun grading those essays."

She glares back at him. "That's low, even for you Winchester. I'll remember that." She points to her eyes then snaps her two fingers in his direction to indicate she'll be watching him. He just smiles and waves at her with his fingers as he pulls his phone to his ear and continuing down the hall to leave the building.

Sam picks up in a few rings greeting Dean with, "Chinese."

Dean quirks an amused brow pushing through the front doors heading to Baby. "How did you know I was calling about food?"

"Dean," Sam said with a tone that indicates that that was the most ridiculous question he's ever heard. Which, to be fair, it was. It's Tuesday at three pm. "So are you good with Chinese?"

"Sammy," Now it's Dean's turn to use that same tone Sam had just used on him seconds before.

"Right, stupid question." He pauses for a second before adding, "Don't forget the wantons."

"I never forget the wantons, unlike somebody who conveniently forgets to get the pie."

"That was one time, Dean, let it go." Dean can hear the eyeroll in his words. "I got you cake instead, okay. It's practically the same thing."

"I don't think we can be brothers anymore. I have never been more disappointed in you in my life." He opens the doors to the Impala and slides in, placing his bag on the passenger's side before closing the door, then under his breath says, "Practically the same thing."

"Yeah, yeah, it isn't the first time. Just hurry and order, I'm starving. I have to go now though if I want to finish this paper before the show starts."

"Okay, I'll-" Sam hangs up on Dean making Dean blink a few times before lowering the phone. "See you in a bit." Sam has always been like that when he's focused on his work, he doesn't mean to be rude, but damn if he doesn't come across as an asshole sometimes.

Pushing that aside Dean calls the chinese restaurant and places their order before starting his car and making his way back to his house. The whole way there he is bouncing in his seat and singing along with the music, hitting the steering wheel to the beat, but careful to pay attention as he drives. At one point during the drive when he stops at a stop light he points over to the person stopped next to him, making sure their window is down first, and starts to serenade them. Life is too short to care what others think, at least when it comes to jamming out in his car on his way home.

Finally pulling into the driveway he gets out and locks her up heading inside. It's quiet, but that's to be expected since Sam is most likely still working on his paper. Knowing this, Dean stays respectful and remains as quiet as he can since he knows Sam works best when there is no noise.

He kicks his shoes off and throws his bag on the couch in front of the television, then he strips his belt off and heads back to his room getting into some more comfortable pants. Now in more fitting attire for the evening, Dean makes his way back into the living room to plop down on the couch alongside his bag and throws his feet up on the coffee table. He pulls out the papers and his favorite red pen, clicking the end and starts marking up the papers.

When he's nearly done with grading the papers the doorbell rings, and there can only be one reason for it. Chinese is here. Had he really been grading for that long? Going to get up he stops when he hears the door opening and Sam's voice following. Pivoting himself, throwing an arm over the back of the couch he watches the exchange. Sam closes the door and turns to Dean holding up the food with a smile walking over and plopping next to his brother.

Dean sets the last of his papers aside and he and Sam divvy out the food. "You get your paper finished?" Dean asks leaning back into the couch with his container of delicious chinese food, ready for Mishapocalypse to start anytime now.

Sam groans rubbing his neck reaching for the remote to turn on the tv. "No. This paper is killing me and it's due Friday." Sam's eyes glance at the papers next to Dean then smiles up at Dean. "I take it you haven't finished your papers either?"

Dean groans as well. "No. Remind me to never have them write a paper again. I regret even thinking about it."

Sam lets out a soft chuckle changing the channel to the one Mishapocalypse is going to play on in five minutes. "You're an English teacher, Dean. They're bound to write at least one paper."

Dean stuffs a forkful of rice and chicken into his mouth glancing to his brother. "Yeah, remind me again how the hell that happened."

Sam shrugs settling back. "It was your idea, I stopped questioning your thinking a long time ago. You mentioned wanting to help the kids."

"I was stupid." He huffs. "Students don't listen to their teachers. I of all people should have known that."

"Is that Carlos kid still causing issues?" Sam asks raising an inquisitive brow.

"I don't think he'll ever stop. He may just be a lost cause."

Sam frowns. "You know, a lot of people thought that about you too." He turns his eyes to his brother's. "Then Sonny came along and brought you to your senses." Sam scoffs moving his eyes back to the tv, eyes creasing with the lines of a smile. "And thank God for him, I had no idea what to do with you anymore."

Dean rolls his eyes with a lighthearted scoff, but a small smile breaks through. "I owe a lot to Sonny," Dean sighs knowing what Sam was implying through bringing up Sonny, and he drops his eyes to his food on his lap. "But I don't think I'm the best person to be telling those kids what's right and wrong seeing my past was … less than admirable."

"It's because of your past I know you can do it, Dean."

Dean brings his eyes to his Sam's green ones and he sees the truth in them. Sam's expression is so genuine that Dean has to look away, feeling the moment is too candid and raw for his liking, and Dean has never been one for mushy moments like this. But thankfully they don't have to sit there long in the silence because Mishapocalypse decides it's time to start.

Doing his best, Dean tries to stop thinking about his life and that he most likely made the wrong choice like he always manages to. Because knowing him he is going to ruin the kids' lives rather than help them like he wants to do, and he is too old now to go back to school and go down a different path.

His eyes are locked on the tv trying to watch it, but his mind is swimming with regret, like it always is. One the tv there is a woman walking fast paced down a hallway in a business suit and briefcase in hand, but the camera is panned down so the viewers cannot see her face. Dean doesn't know her, but the way she holds herself high and confident is enough to catch his attention a little more. The screen flicks to a scene in a courtroom and shows a judge in the podium.

The judge lifts his gavel saying, "I hear by find you guil-"

The doors burst open and the women stopping him mid-sentence and causing everyone in the room to spin their attention to the intruder. The blonde women confidently and loudly states, "He is innocent."

The judge slowly lowers his gavel with a small glare. "And who are you?"

"Adrianne, your honor,"

The screen changes to a different scene indicating the end of that one. The new scene is a familiar one, the FBI office. Sitting there at his desk is the familiar black haired, blue eyed man, he is leaning back twirling in his desk chair.

Matt, Misha's boss, also Castiel's real life older brother, Michael, steps out of his office and stares in Misha's direction. "Misha."

Misha stops his spinning, flashing the smile that makes Dean heart skip a beat. "Matt," Misha stands up with a stretch, arms locked rising above Misha's head making it so some of his skin shows. "About time you came to your senses and gave me another job."

' _The directors did that on purpose.'_ Dean grumbles to himself.

Misha makes his way towards Matt and pushes into this office. Matt sighs closing the door behind them. "After what you did on the last mission I had the mind to fire you, Misha, so don't go acting all high and mighty."

Misha smiles at him tapping a finger on his desk taking a seat in the chair facing Matt's desk. "But you didn't fire me."

Matt grubles and sits at his desk, fixing Misha with a stern glare. "Misha, the only reason you are getting another mission is because this one is so dangerous you are the only one I trust to get it done right without dying."

Misha's smile falls and he turns oddly serious giving Dean chills at the drastic change. Castiel is such an amazing actor, anyone who claims to not like him clearly haven't seen Mishapocalypse. Sure his older stuff is good too, but he has had years to refine his skill and he is at his best in Mishapocalypse.

"What is it?" His voice even lowered into something more serious making his voice almost have a sexual tone to it. It's gravelly and deep, and it should be illegal.

Matt simply stares into his blue eyes leaning back in his chair folding his hands over his stomach. "We found them." Misha thins his lips and nods not saying anything, a far off look in his eyes. "If you can't detach yourself from it, I can have someone else do it."

"No." Misha meets his eyes, all hints of anything that was there before is gone only leaving determination. "I will do this." He gives Matt a smile. "I'm going to take pleasure in taking those fools down."

Dean bites his lip getting nervous. It's the gang who tortured and killed his wife from season one, the only family he had left. It broke Dean's heart watching Misha tear himself apart for not being able to save her. He says he's over it now, but everyone knows he will never get over it.

As the show continues it cuts back to the lawyer from the beginning, Adrianne. Dean quickly took to liking her. She seems to be struggling with something and her one friend is trying to tell her that maybe it is best to leave it alone, what 'it' is exactly Dean doesn't know, but he is curious.

Nearing the end of the episode, it fades to Misha's bedroom. The camera is directed to a pair of feet in some fancy, sleek, black shoes. As the camera pans up it reveals Misha in a suit fixing his tie in front of a mirror, hair slicked back, stubble on his face. He must be getting ready to go undercover. He is looked like a respectable, sophisticated man, but he is now a mafia leader.

Misha smiles at himself in the mirror running his hands over any imperfections in his suit to straighten them out, he then runs a hand over his face so he isn't smiling anymore. The look in his eyes gives Dean the chills. Just like that, Misha looks like a completely different person, almost cold. It's as if he and his old self got a divorce and now it's a completely different man. His acting skills are impeccable.

The scene fades back to Adrianne and her friend again.

"Adrianne, have you even thought this through? He could be a psychopath or something, really, maybe you should just forget about him. Plus, he probably doesn't even know you exist."

The blonde glares back to her friend. "Alex,"

"I know, okay." She sighs rubbing her face exhausted. "But Adri, you and the police have looked for years. Don't you think you would have found something by now?"

"I'm going to find Dimitri," Adrianne straightens up looking Alex in the eyes. "I'm going to find my brother." And at that, the scene fades and the credits start to roll.

Dean and Sam both sit there for a minute. Dean's face scrunches, mind reeling as he says, "Who is Dimitri? And what is Adrianne's role in all this?" He keeps his eyes on the screen of the tv for a moment waiting on Sam to respond, but the longer the silence drags on Dean realizes Sam isn't going to answer. Dean arches a brow and glances over to Sam. "Sammy, you good?"

Sam looks as if he was just handed a rather difficult calculus equation and told to solve it without a calculator, his brows knit together, eyes narrowed, lips pressed close together. Dean wants to say something but he doesn't want to interrupt his thought process. Is he thinking about Mishapocalypse?

Just as Dean is starting to get worried Sam's eyes slowly widen and he whispers, "Jess?"

Okay, now Dean is completely lost. Who the heck is Jess? "I was starting to think you froze like that and I was going to have a statue as a brother." Dean sighs leaning back on the couch. "Who's Jess, some girl in your class or something?"

Sam looked over at Dean, body pivoting to face him, one leg coming up to rest on the couch. "No, Dean, Adrianne," Sam points to the screen where the next show has already started. "She is Jess. Jessica Moore. My middle school crush."

Dean's eyes snap wide staring into his green eyes. "Heart throb Jess? The girl you were head over heels for? _That_ Jess?"

" _That_ Jess."

Dean's eyes glide back to the television's screen as if her picture is plastered on it. "Holy shit…" His voice is just above a whisper. He rubs his chin in thought and nods with an appreciative look. "I always knew she'd turn out hot."

"Dean." Sam groans. "Is that seriously the only thing you have to say?"

Dean meets his angry eyes and realization hits him. "You still like her."

Sam scoffs standing up grabbing their empty chinese containers to throw them away. "No, I don't."

A smirk spreads itself across Dean's lips as he stands up following Sam into the kitchen to throw his own container away. "Oh Sammy, you have it bad." He chuckles.

Sam narrows his eyes at his brother. "I admit I liked her back when I was in middle school, but I don't know her anymore." He shrugs leaning his butt against the counter crossing his arms over his chest. "Besides, she probably doesn't even remember me. Hell, she has people probably throwing themselves at her all the time now and I'd look pathetic trying to contact her now only after I found out she's an actress."

"There's no way she could have forgotten someone like you." Sam looks up with a shocked expression. Dean isn't making a joke about it and he is actually being nice, he wasn't expecting that. Dean shrugs. "You were such a goofy looking squirt I'm sure nobody could forget you."

There it is.

Sam rolls his eyes remembering why he doesn't confide in Dean very often, and it probably would have been best if he kept the Jess thing to himself. Telling him only gave him more fuel to tease him about. "Forget it Dean. I have a paper to write." Sam pushes off the counter and heads up the steps to his room.

"Sam," Dean walks to the bottom of the stairs watching Sam's back as he closes the door behind him. "I was kidding. Sam, come on." Dean sighs rubbing the back of his neck staring up the stairs waiting to see if Sam will come back out, but he knows he isn't going to. He'll get over it, he always does. All he needs is a little space, so that's what Dean gives him.

XXXXX

{picture of Castiel}

Caption: Castiel appreciation post! Thank you for being here and doing what you do best! Love you Castiel

Comments · Order by **Oldest to Newest**

 **Casteil_Misha** · 2 hours ago

*eternally cries over Castiel because we don't deserve this man* I love him so much T-T

 **Imp_ala** ·2 hours ago

I will follow this man to the ends of the Earth, all bow to our overlord and savior Castiel!

 **Death_is_my_homie** ·1 hour ago

I don't think Cas ever thought he would end up being called an overlord lol, I wonder if he knows what he has created

 **Cassie_my_man** ·48 minutes ago

I love this man. Castiel, what have you done to me? D;

 **CasCasNovak** ·35 minutes ago

I finally get to meet him at the convention in a week and a half! I am so happy I finally get to meet my idol T^T

View more comments

XXXXX

Not long after his little argument — if you can call it an argument — with Sam, Dean decided he needed to get out of the house to finish grading those damn papers. He tried doing them on the couch but he just couldn't concentrate, so what better place to clear his mind than his favorite little late night cafe, Gabe's Coffee. The cafe that Dean in currently sitting out front of in Baby. The cafe has some of the best coffee Dean has had in a long time, and it is the only coffee that can actually keep Dean awake through grading papers. He has to admit, at first he only came to check out this cafe because he heard Castiel's brother was its owner, but after coming here he actually found he liked the shop.

Dean pushes through the glass doors to the cafe and the smell of coffee instantly fills his nose. He smiles walking up to the counter where Gabriel is standing.

"Dean-o, it's been a while, what brings you?" The brunette greets him with a cheerful smile, and putting his hand on his hips.

"Oh, you know," Dean pats his bag with the papers in it. "Work."

Gabriel scrunches up his face. "More papers?"

"Yup."

"You're gonna need the special, aren't you." He says this as a statement more than a question because he already knows the answer. "I don't know how you do it." Gabriel shakes his head and takes Dean's money.

"I don't even know how I do it some days."

Gabriel laughs and starts to make his drink. There aren't many people in the cafe right now seeing it's decently late, but there are a few people here and there. His attention is drawn back when Gabriel slides his drink to him with a smile. "Well, I'm glad you're doing it so I don't have to. I admire your desire to change the younger generation, even if it is futile because children listen to nobody."

Dean takes the cup rolling his eyes. "Tell me about it." He does a motion of a toast saying his thanks to Gabriel before heading over to a table by the windows and getting settled in. As much as he doesn't want it to be, it's time to get crackin.

While grading papers can be very tedious and aggravating at times, sometimes he comes across some sentences, or even whole papers, that just crack him up and make them worth it. He honestly should let them do personal essays more often. The bell above the door jingles indicating a new customer, but he doesn't look up from the paper his eyes are glued to seeing it's one of those rare moments that make it all worth it.

He hears Gabriel talking to the person that just walked in, but he can't hear what they're saying. Dean takes a sip of his drink leaning back in his chair, then he hears Gabriel's voice directed at him. "You're having too much fun over there for grading papers, Dean."

Dean grins. "If you read this essay you would be laughing too." He takes another sip and looks up to Gabriel, but when he sees the other man standing there smiling over at him, Dean chokes on his coffee. He lurches forward coughing sporadically in attempt to be able to breath correctly again. He hears some voices but he can't focus on them, his mind being bogged with other thoughts. Once his coughing slows he hears a familiar voice, one that he usually only hears on the television.

"Are you alright?"

"Yeah, I, uh…" Holy shit his voice is so … no, he's not going to finish that thought. He slowly sits up rubbing his throat trying to get all the inappropriate thoughts from his head because he isn't supposed to think of a man like that. His father has made that clear to him at a young age. He looks up and meets a pair of captivatingly blue eyes, all thoughts wiped from his mind. "Whoa…" Castiel furrows his brows a bit and tilts his head to the side waiting to see if he's alright. Dean's voice is almost a whisper as he says, "Your eyes are beautiful."

Castiel's eyes widen slightly not expecting him to say that, but soon he smiles.

Realizing what he just said Dean's eyes fly wide open and he feels his face grow hot. "I, sorry, I didn't, they're just … really blue." Dean fumbles for his words and tries to cover it up, but he only succeeds in making himself even more embarrassed. There is a moment of silence and Dean thinks he royally messed up his first ever meeting with Castiel, but the next moment he braves a look at the man. His eyes are crinkled and the corner of his lips are turned up in a smile, then before he knows it there is a small laugh that comes from Castiel and it makes all his embarrassment worth it.

He meets his eyes, smile still in place. "It's alright." He assures Dean. Now typically at this time Dean would look away from the person's eyes, and he should want to look away not wanting to stare at him and be rude, but he can't. Their eyes remain locked for what feels like minutes, but in reality it's only a few seconds, and they stay like that until Gabriel's voice breaks them apart.

"Now would be the moment to comment on his eyes, with as much as your staring into them." They both simultaneously break eye contact. Castiel narrows his eyes at his brother and Dean drops his eyes to the papers for a second before looking back to Gabriel. "What?" Gabriel asks with a small smirk. "It's common courtesy."

"Gabriel." Castiel says with a stern tone.

"It's fate at first choking." Castiel and Dean's eyes both widen at the man and Gabriel shrugs as if it's no big deal. "For Dean-o and I it was fate at first coffee, I get that feeling, you know?"

Neither Castiel or Dean know what to say about that. Dean tries to think of something, but he only succeeds in making himself resemble a fish, but luckily neither of them have to say anything before Gabriel speaks up again.

"So, Dean, you going to the convention next week?"

Dean's mouth closes and he furrows his brows, and from the corner of his eye he sees Castiel turn his eyes to him. "What convention?"

Gabriel rolls his eyes and crosses his arms, clearly not buying that Dean had no clue what he is talking about. "Oh, come on, I know you're a fan of Mishapocalypse from the reaction to seeing Cassie here. There is a convention for it next week, don't tell me you didn't know."

Dean's eyes widen, he actually hadn't heard about any convention. But now he is feeling oddly nervous because now Castiel knows he is a fan of his show. He doesn't know why that makes him nervous, but for some reason he feels Cas is going to look at him differently now. Although the convention would be a great present for Sam for his birthday. He would be able to meet Jess again. At that thought he freezes, that's perfect.

Castiel's eyes snap to his brother with a glare for putting Dean on the spot like that. "Gabriel."

"What? I'm curious." Gabriel shrugs.

"Are the tickets still being sold?" Dean asks making both of them to turn their attention to him. "Okay wait," Dean purses his lips in thought trying to put them together so it doesn't come out rambled. "I'm new to the whole convention thing,"

"You don't say." Gabriel mocks, earning a glare from his brother, but Dean pays it no attention.

"Do we get to meet the actors if we buy the tickets?"

"There are a couple different types of tickets. There are the normal admission where you won't get to get autographs and you won't get any photo ops. If you want to meet the actors then you would have to buy the silver ticket at least, but even then you won't get to meet all the actors."

"Is Jessica Moore going to be at this convention?"

Castiel nods, the faintest flicker of disappointment flashes across his eyes when Dean smiles widely. "Yes, you will be able to meet her with the silver ticket. I can get the ticket for you if you'd like."

Dean's eyes widen at the offer. "I couldn't ask you to do that, I can get them online right?"

"It would be no big deal, but yes you can get them online."

Dean relaxes a bit. "Awesome, okay, uhm," He starts packing his things and slings his bag over his shoulder looking back up to them. "Thanks for the coffee as usual Gabriel, and uh," His eyes meet intense blue ones and he has to take a moment because _damn_ they are so much prettier in person. "It was really great meeting you, like," A wide smile spreads across his face and he is unable to stop it as he says, "Awesome, but I have some tickets to buy. See you later."

Dean starts heading to the door and Gabriel pipes in before he leaves, "Gold ticket meets Cassie by the way."

"Thanks Gabe." Dean shoots back over his shoulder as he pushes through the doors.

Castiel narrows his eyes at his brother walking back over to the counter. When Gabriel meets his eyes he smirks. "If you keep your face like that it's going to stick eventually."

"What are you trying to get him into, Gabriel?"

"Why do you always think I'm plotting something? Can't I just do something for my best friend without you criticizing me?"

"No." Castiel sighs, shoulders sagging. "Gabriel if you are trying to play matchmaker again-"

"I'm not." He cuts in. When Castiel gives him a skeptical stare he elaborates. "I promise, I was just telling him the gold ticket met you because you left it out."

Castiel arches a brow, but decides to let it go. "Fine, but I feel I have to re-inform you I am perfectly happy with my life how it is now."

Castiel pulls his bottom lip between his teeth for a second thinking about Dean. It felt like they had a moment when they were looking into each other's eyes, but Castiel has to assume Dean only likes him as Misha considering Dean doesn't really know him. But who is Castiel to say Dean even likes men in that way? Dean probably was just excited to meet Castiel because he is a fan, and Castiel was just projecting his own desires into Dean's eyes.

Okay, so Castiel really does want to be in a relationship with someone, and he is actually trying to find someone, but it is so difficult. Besides Dean is probably straight, judging from the reaction he had when Castiel said Jessica would be at the convention, which kind of sucks seeing he seems like a really nice person, but he will just have to get over it.

Gabriel frowns for a second seeing the look in Castiel's eyes. If someone didn't know him like Gabriel does, then they wouldn't see that disappointment sitting there. Gabriel has known Dean for a while now and yes they only talk when he comes in the shop, but they have had a few meaningful conversations over the year, and Gabriel would like to think he's gotten a good reading on Dean's personality. Sure Dean appears straight, but Gabriel has learned to not assume things about people when Castiel came out to him.

Or perhaps 'came out' isn't the right term in Castiel's words, he said he was never 'in any closet' and Gabriel simply assumed what he was.

So long story short, Gabriel doesn't assume anyone's sexuality anymore. He needs to hear it from their lips for it to be concrete. Also meaning Dean seems straight, but he could be bi, pan, or anything under the rainbow. Another possibility is that Dean doesn't know what he likes and only goes after women because that's the normal, and all he could need is a little nudge in the right direction, preferably with his brother so Castiel will stop making those puppy eyes at all the couples he passes and making Gabriel, the overprotective older brother he is, worried as fuck and just wants him to be happy.

Castiel has left Gabriel no choice but to play cupid again. There is no way he is going to make any kind of move on Dean, so this mean he is going to have to crack out some ingenious ideas, and fast. He is going to put this plan into action at the convention if all goes well.

XXXXX

Dean slides into the driver's seat to the impala and starts her up. His eyes dart over to the cafe for one more glance and sees Castiel talking to Gabriel through the storefront windows. In that moment realization washes over him like a freight train.

He just met Castiel Novak. He just choked on his coffee and Castiel asked him if he was okay. Castiel's eyes were on _him_. They had talked as if it was a normal occurrence. Dean just met Castiel _fucking_ Novak by pure luck.

"Oh my god…" He whispers to himself as he runs his hands down his face. He never thought he would be thinking this, but he is so happy about having that little spat with Sam right about now.


	2. Chapter 2: Lost Papers

Thank you to everyone who favorited, followed and reviewed! It lets me know you enjoy this story and I'll keep writing it, so don't feel shy about reviewing. I promise I won't bite xD

Just in case you wanted to see the pictures/read it on AO3, this is where you can find it (Just replace dot a period): **AO3 dot /works/12218790/chapters/27752979**

* * *

 **Chapter 2: Lost Papers**

When Dean pulls into their driveway, he is still awestruck with the happenings a few minutes ago. He gets out of the car and wanders into the house in a slight fog, going through the actions purely on reflex. Trying to get himself together he rubs a hand down his face kicking off his shoes, shrugging off his jacket, and hanging up his bag. Dean glances at the clock on the microwave and glaring back at him with bright green numbers it reads nine o'clock. He rubs the back of his neck and makes his way over to the stairs and looks at Sam's door. The light to his room is still on, but Dean knows he shouldn't bother him, he's still writing the paper most likely. Not to mention he's also most likely still a bit angry at Dean, so instead Dean heads up the stairs and into his room across the hall.

When he gets in his room, he gently closes the door and sits down on his bed grabbing his laptop and firing it up. He navigates the internet and pulls up the official site where the tickets should be sold at. His eyes scan the screen and when they finally land on 'TICKETS' in bold letters at the top, he clicks on it. He scrolls down to the prices and nearly chokes on the air he's breathing seeing the ungodly amount of money he is about to fork over. There is no way he is going to be able to afford two bronze tickets let alone two silver.

The thought crosses Dean's mind making him question whether this is the right thing to be doing. There are much more important things he could do with that money than to be buying tickets for a convention and, what, maybe five minute celebrity interaction time?

But then again, this would mean the world to his brother, finally being able to talk to Jess again. Hell, he would be happy with just being able to see her in person again, even if he didn't get to talk to her. The smile that would light up Sam's eyes would all be worth it, and with that thought, Dean decides he is buying the ticket for his brother. Even if it means Dean will have to cut back on eating for a little while, it's worth it to see Sam that happy.

He adds the silver ticket to his cart and hesitates for a moment. He doesn't have enough for two silver, not even enough for a silver and bronze. Although that's fine because Dean doesn't need the photo ops and autographs, he will be content with simply being there to witness the magic with his brother. Sam, on the other hand, might be a little upset that Dean spent that much money on him, but it is his birthday so it's okay. If it were up to Dean, and yes in a way it is, Dean would forgo his own ticket, but Sam wouldn't have any of that. He would be pissed that Dean isn't going because he knows how much Dean loves the show too, so not buying a ticket for himself is out of the question considering this is supposed to be a way to make Sam stop being angry at him in the first place.

Coming to that conclusion, he adds a normal admissions ticket to the cart and checks out, cringing at the price it comes out to. When it's all said and done, and he prints out their tickets, he closes the lid on his laptop setting it on his nightstand and heading downstairs to grab the tickets.

It's the moment the tickets are in his hands that Dean realizes Sam could possibly have something going on next Friday, Saturday, and Sunday, and he pauses. What if he bought these for nothing? He thins his lips and shakes his head folding up his normal admissions ticket so he can't see what it is and magnets it on the side of fridge for safekeeping — also putting it in a spot that Sam won't second guess why there's a paper and gets too nosey for his own good, sneaking a peek at what's inside. As for Sam's ticket, he folds it into threes and slides it into an envelope, sticking it under the same magnet as his ticket. He will give it to Sam tomorrow even though his birthday is in three days.

Honestly, this convention couldn't have fallen on a better date, and the fact it's only a thirty minute drive from where they live is awesome.

Taking one last glance at the tickets, he heads upstairs to hit the hay for the night. He shouldn't worry about Sam finding the tickets, it's only until tomorrow night.

XXXXX

Dean is startled out of his beauty sleep by his alarm clock screaming at him right next to his head. A giant hand slams down on the black clock, taking a few swats before successfully silencing its obnoxious screeching. Dean groans and stretches, a small moan escapes him in doing so. Laying there for a minute longer, the smell of coffee is what encourages him to swing his legs over the bed, out from the warmth of his blankets and get his day started.

After getting around he makes his way downstairs, following the smell of the coffee his brother brewed for them. Standing in the kitchen is the younger Winchester, leaning against the counter, still in his pajamas, coffee mug in hand.

Sam looks up from over the top of his mug with bleary eyes, indicating to Dean he hasn't been up long either, and a small "Morning." coming from tired lips.

Dean nods fighting off a yawn and losing as he grabs a mug and pours himself a cup. He rolls his neck taking a seat at the dining room table, which is basically in the kitchen. It's a small table, it could fit four if need be, but it comfortably fits two. Perfect for him and Sam.

Only when Dean takes a couple sips of his coffee does he realize Sam doesn't usually wake up before him. He arches a brow, eyes falling on the microwave clock reading 7:20, then he looks to his brother. "Why are you up this early? Your classes don't start until nine."

Sam finishes his first cup and pours another before answering Dean's question, deeming it too tasking to even try and hold a conversation until he has had at least one full cup of coffee. "I have to go in early today for a mock trial. I'm one of the lead lawyers in the case, so I want to make sure I have everything ready before I go."

"Mock trial? This early?" Dean pushes out air in an exasperated motion. "That's rough."

Sam hums with a faint smile. Sam seems to be acting normal towards Dean, which Dean was expecting, but it is still a relief knowing Sam isn't still angry at him. Their little spats don't typically leave them angry at each other for very long afterward, as long as the other leaves them alone for some time. The longest their argument lasted have been a few days, but that was when they were kids and would like to poke the bear with a stick just for shits and giggles. Now both of them are adults and handle these kinds of situations much better. They both know they need space, and poking the bear now could lead to injury, or worst case scenario, the hospital.

"So," Dean starts, deciding to put some nerves at rest so his brain will be able to focus today instead of worry needlessly. "Have anything planned for this weekend?" He stands up when he finishes his coffee and rises it out before setting it in the sink for cleaning later, then heads over to the fridge grabbing something for lunch, then goes to the door getting ready to leave.

Sam thinks it over for a moment before answering again. "I have to study for some tests, but other than that I don't know. I might head out with some friends, just hang out." Sam arches a brow at Dean confused because Dean doesn't usually ask unless he has something planned. "Why?"

Dean shrugs as if it's no big deal, sliding on his leather jacket, shoes, bag and grabbing his keys. "Nothing big, just, don't plan anything that can't be done from a hotel room."

Sam's brows furrow together as Dean opens the door. "What? Why?"

"We have plans, Sammy." Dean walks out the door and smiles back to Sam in the doorway when he reaches the Impala, throwing his things inside. "You, me, and Baby here. Birthday boy's weekend."

Sam's eyes widen in realization that Dean most likely went overboard for his birthday again. "Dean, how many times do I have to tell you that you don't have to make a huge deal for my birthday? You can use that money for-"

"Sam, shh." Dean puts a finger to his own lips to silence his brother, a smile tugging at the corners of his lips seeing Sam have a petulant look on his face. "It's already done, so just enjoy it, 'kay? Okay. Now I gotta go, knock 'em dead today, Sammy!" Dean gets in his car and pulls out of the driveway.

Sam still standing in the open doorway watching his brother leave whispering a petulant, "It's Sam." to himself.

XXXXX

The beginning of the day is same old, same old. Classes are boring, students are rowdy and rude, and his brain is off in la-la land. He has tried to focus and is doing a decent job, but the longer the day drags on the more he is on cloud nine over last night's events.

He tried to forget about it so he can be professional, but he met his favorite actor. That isn't easily forgotten, and really he doesn't want to forget it.

By the time lunch finally strolls around, he makes his way into the teacher's lounge, ready for a little R&R. He grabs his lunch from the fridge and plops on the couch, ready to eat. That's when a familiar red-headed girl walks through the doors in her typical energized manner.

"What's up bitches." She winks at Dean twirling her bag of lunch on a finger as she sits next to him on the couch. "Wonderful morning, isn't it?"

Dean can't help but crack a smile at her. "You know, it isn't setting a good example for the students when you swear like that."

She rolls her eyes at him. "Dean, we all know you swear like a sailor."

Dean scoffs. "Nobody ever said I was a good role model, if they did then they were clearly delusional."

"Have you forgotten what I do?" She raises a brow meeting his eyes. "I'm a hacker, Dean."

"Trust me, I haven't forgotten." Dean glares over at her, but she knows the look doesn't have malicious intent. "Have you forgotten you hacked my laptop a few months ago because I wouldn't tell you the new show I was watching."

Charlie smirks at the memory. "It's your own fault. You should have just told me you were watching Mishapocalypse. I wouldn't have had to snoop through your search history on google and find all the pictures of Castiel you were looking up."

"It was that new addiction phase, okay. Everyone looked up pictures of their favorite show when they get addicted to it in the beginning." He argues, probably a little too defensively.

Charlie simply hums, a smug smile on her face as if she can see right through Dean. "Whatever you say, big boy. Whatever. You. Say."

Dean debates for a second whether or not he should tell Charlie about what happened last night or not. He doesn't want her to make a big deal over it, but on second thought, holy shit he has to talk about it or else he is going to explode! He would have told Sam this morning, but it was the morning and he was too tired to even think about starting such a high energy conversation that early in the morning. And the fact that Charlie is really the only one who knows just how obsessed he is with the show, since she hacked his laptop and discovered all his secrets, so when he is talking about the show, she is the only one he feels he can be truly himself around. Hell, he even hides some of it from Sam. So he finds himself breaking down to spill, nearly, everything about last night.

"Something happened to me last night." This sentence successfully catches her attention and her playful attitude dissipates. "I still can't wrap my head around the whole thing, it was really…" Dean blows air out his mouth and motions with his hands that his brain is exploding.

"What happened?"

"I was in Gabe's Cafe last night after having a little fight with Sam, and that's when Castiel walked in." Her eyes slowly widen and her mouth slacks open slightly. "I got to meet him because I choked on my coffee."

Charlie snorts a small laugh at that, but she is still in shock. "Get. Out."

Dean nods. "I know right?"

A smile gradually grows on her face until she is practically a lighthouse. "Get out! No way! Oh my god, Dean!" She repeatedly smacks him on the arm lightly, bouncing where she sits. Dean smiles at her and she collects herself, turning to face him, ready for the gossip. "Okay, Winchester, give me all the deets. Leave nothing out. Was he just as attractive in person as on TV?" Dean arches a brow at that question since she made it very clear that she isn't into men. She sees this and rolls her eyes. "I may only be into girls, but I can appreciate attractive men."

Dean chuckles at that but nods his understanding. "Yeah, well, he may be attractive on TV, but in person?" Dean whistles and chuckles. "I may be straight, but I can appreciate attractive men when I see them. And oh boy, his eyes were something else." He meets her eyes and raises his brows for emphasis. "Bluest eyes I've ever seen. Seriously, you could get lost in those suckers."

Her eyes crinkle as she keeps smiling, listening to Dean explain everything that went down last night. From grading papers to purchasing the convention tickets.

"I'm so jealous." She grumbles. "I want to go to a Mishapocalypse convention." She sighs resting her cheek on the heel of her hand. "So, what hotel are you going to be staying at? Unless you're staying at home since it isn't far away."

"We're going to be staying at a hotel, I found a cheap, but classy, place that is only a few minute walk from the convention. Figured it would be more of an experience this way." Dean shrugs. He wasn't going to rent the room, but it wasn't expensive and he wanted to make the most of this whole event, plus Dean didn't want to risk getting caught in morning traffic on the way here every morning. Better safe than sorry, right?

After lunch ends the day seems to drag on longer than usual. All he wants to do is get home and give Sam the ticket. Nearing the end of his last period, he gets to hand back the papers he finally finished grading last night at the cafe.

"Okay, class, I finally got your papers graded. I'm going to hand them back so you can see your grade, but I'm going to need them back to put them in the grade book." Dean grabs the pile of graded papers and starts handing them back. When he starts getting closer to the end of the pile he realizes that there aren't enough papers for the number of students remaining. His eyes widen realizing he lost some papers. He thins his lips and hands out the remaining papers before speaking up. "I apparently left some of your papers at home, but I promise I'll get them to you soon."

The kids that didn't their papers groan but the bell rings indicating the end of the day. The class stands, and those who got their papers returned walk over to Dean's desk and set their papers on it before scrambling out the door. Dean sighs when all the students leave and he follows suit after he gets his things. When he is sitting in his car driving home, he is trying to think of where he could have possibly left the papers, and that's when he realizes he could have very possibly left them at Gabe's Cafe. He wasn't exactly thinking straight at the time and could have very easily overlooked a few papers.

He decides he will go to the cafe after he talks to Sam and gives him his birthday present, it will still be there by the time he finishes talking to him.

Dean pulls into the driveway and puts his car in park, making his way to the door. He isn't sure if Sam is home already or not because Dean doesn't know how mock trials work or how long they take, so when he opens the door and sees Sam's sneakers laying there he is a bit surprised. Dean hangs his things up and kicks off his shoes peeking his head around the corner of the kitchen to see if Sam is there before walking in and over to the fridge. Sam must be in his room.

Dean is relieved to see the envelope hasn't been touched, even though he knew it was going to be fine, there is still that possibility that Sam could have found it. Dean turns so he's facing the archway to the kitchen and leans his butt on the counter.

"Hey, Sammy! If you're not busy right now I want to talk to you about something."

After a second Dean hears Sam shuffling around upstairs, soon followed by the opening and closing of his door and the patting of socked feet on the stairs. Sam appears from behind the wall looking a little nervous and confused. "What is it?"

Dean chuckles at the almost scared expression in his brother's eyes. "You have something I should be worrying about? You look petrified."

Sam corrects himself and rolls his eyes. "No, but whenever you ask to talk, well, you know what happens."

Dean scoffs at him. "I just wanted to give you your birthday present. I know it's early, but I don't care." Dean holds the envelope out to Sam and flaps it a couple times before Sam skeptically takes it.

Sam's eyes stare at the white envelope for a few seconds, probably trying to guess just what could be in it, before bringing his eyes back to meet Dean's green ones. "Dean,"

"Just open it." Dean cuts in before Sam can go on a lecture about how Dean should have saved his money and yadda, yadda, yadda.

Sam purses his lips a bit, still wanting to say what he was going to say. "I just know we are in a tight spot right now and I don't want you to feel obligated to go overboard like you usually do."

"I don't go over-" Sam cuts him off with his famous bitch face and Dean shrugs a bit. "So maybe I go overboard a little, but you're my brother so it's allowed. Besides, I've been saving up for this for a while now, so don't be a buzzkill." Yes, that is a lie, but what Sam doesn't know won't hurt him. Plus, they have enough money to get by until next paycheck even with spending that money on the tickets.

Sam mumbles, "I'm not a buzzkill." as he flips the envelope over and begins to tear it open. When the top is open Sam pulls out a paper and unfolds it, reading over what it is. All of a sudden Sam nearly chokes seeing what it is and knowing how much it cost because he has looked them up before. Collecting himself he brings wide eyes to Dean, and the smile on Dean's face is enough to stop Sam from mentioning anything about money. Dean's face lights up a little more seeing Sam loosen up and actually smile at his brother.

"So you like it?" Dean asks as if he doesn't already know the answer. Because he really doesn't know, Dean was so nervous that Sam would be upset at him for spending that kind of money and hate the gift.

"Like it? Dean this is the best present ever." Dean's shoulders sag in relief and Sam laughs, dropping his eyes back to the paper and that's when he realizes there is only one ticket. He scrunches his brows together and meets Dean's eyes again. "There's only one ticket, aren't you coming?"

Dean nods knowing this was going to happen, he was just waiting for it. He nods his head towards the fridge, "Mine is on the side of the fridge. It's just a normal admissions ticket though." And before Sam has time to chime in, Dean thinks now is as good a time as any to tell him about that thing. "Besides," He starts, successfully stopping Sam's thoughts. "I already got to meet Cas yesterday at Gabe's Cafe."

"Wait, what? How could you not tell me this morning?! Dean holy crap, seriously?!"

Dean's grin widens. "I'm always serious, Sammy. I wanted to tell you this morning but it seemed like an afternoon kind of talk." He shrugs pointing to the ticket on the table that Sam has momentarily forgotten about. "Plus this conversation goes well with that ticket. You're going to get to meet Jess again."

As soon as the words leave Dean's mouth, Sam freezes on the spot. He hadn't connected to pieces together. Sam is going to get to meet Jess again, in person, face to face, he has dreamt of this, but he never imagined it would ever come true.

Dean watches his brother have a mental crisis, and he has to admit it is pretty entertaining, but the he sees that Sam has stopped breathing and the funny moment leaves. Dean reaches forward now concerned. "Whoa, whoa there kiddo, breathe for me. In and out." When Sam takes a sharp inhale Dean nods patting his shoulder. "There ya go, don't go dying on me just yet. Why don't you sit down?"

"Yeah…" Sam slowly nods and takes a seat at the dining room table. "Okay…"

"Damn, Sammy, if I knew this is all it takes to shut you up I would have done it years ago." Sam only licks his lips and nods, still lost in his own little world. "Did I break you?" Dean waves a hand in front of Sam's face arching an inquisitive brow at him.

Sam pushes his hand down leaning back in the little, very uncomfortable chair. "I'm not broken."

Dean whistles teasingly in relief. "Good, I don't know what I would have told the doctor when I had to take you to the emergency room." Dean looked back at the time and sees now would be a good time to head over to Gabe's Cafe and see if he left the papers there. He slaps his brother on the back with a smile. "While you ponder over what you're going to say to Jess when you meet, I'm gonna skedaddle over to Gabe's Cafe to see if I left my papers there." Dean walks over to the door grabbing his keys. "I'll be back in a bit, want me to pick up dinner to celebrate? Y'know, I'm gonna surprise you, so don't go eating anything." Dean points an accusing finger at his brother who gives him a small smile. "I mean it. No food. I'll be back in twenty." And with that, Dean leaves.

When Dean arrives at the shop, he frowns seeing it look closed. He gets out of the car and makes his way to the shop's windows and sees the little 'Closed' sign hanging on the door. His eyes trail over to the hours sheet on the door and sees the shop isn't supposed to close until six. It's only 4:30, why is it closed? Dean leans close to the glass, cupping his hands around his eyes to better see inside.

He worries his bottom lip between his teeth trying to see if, by some miracle, the papers are just laying around anywhere, but of course they wouldn't just be laying around on the floor. What is he going to do if he can't get them back? He is supposed to be the responsible adult here! But no, of course he isn't. The moment Castiel shows up Dean was head over heels… no, wrong choice of words. That would indicate he has feeling for the man, which he doesn't. Instead, Dean was … distracted and he foolishly lost the damn papers. Stupid, stupid, stupid!

Dean smacks his forehead with his palm and irritably groans, a little too loudly for public because when he drops his hand from his face he sees people staring at him in bewilderment. And just like that, Dean feels like an idiot. Just as Dean turns to get back in his car and hide from the world, he hears a little jingle and a door opening, followed by a voice he never thought he would be so overjoyed to hear.

"Hey, Dean-o, what's got your panties in a twist? You that upset the shot closed early?"

Dean snaps around looking into Gabriel's brown eyes. "Gabriel," Dean sighs in relief. "You wouldn't have happened to find any graded essays laying around, would you?"

A wide smile appears in Gabriel's lips. "I got just the thing for you." He nods towards the open door to his shop. "Come on in." Dean doesn't hesitate to walk past the slightly older man. Once the door is closed Gabriel walks behind the counter and reaches down for his bag and opens it. "I figured you would come back looking for them. Lucky you caught me before I left though." He stands back up and holds out the papers Dean, yet again, never thought he would be so overjoyed to see.

Dean takes him. "Thank, Gabriel." He looks around for a second before looking at him again. "Why are you closed?"

"Ah, well I'm taking a 'vacation' to help out with the Mishapocalypse convention, and I had to close today because nobody that works for me was available right now." Gabriel shrugs but smirks at Dean soon after. "So, I'll see you there."

Dean crosses his arms and tries to play it off as if he didn't buy the tickets, only because Gabriel looked too smug for his own good. "What makes you think I'm going?"

"Oh, I don't know, maybe it's the fact that," He shrugs nonchalantly. "You practically bolted from here as soon as you found out about the convention and you were so distracted that you left your papers here." Gabriel smirks, slinging his bag on his shoulder. "But who knows, maybe it's just me and you bolted for another entirely unrelated reason."

Dean opens his mouth to shoot back a comment, but then realizes he has nothing convincing enough to counter that. The only thing he has would sound made up, which, to be fair, it is. So Dean is left to stand there, arms crossed over his chest, mouth slowly closing, looking like an idiot once again.

Gabriel nods laughing, hand clapping onto Dean's shoulder leading him to the door. "That's what I thought." Once they get outside and Gabriel locks the shop up, he turns to Dean and points two finger guns at him. "See you at the convention."

Dean is left to stand there in front of the cafe, thinking about any kind of comeback that could have saved him that wouldn't have made him sound stupid, but he's drawing a blank. So collecting what dignity he has left, he hauls his ass back to the Impala and goes home to avoid further embarrassment.

XXXXX

 **Hollywood's Top 10 Hottest Bachelors**

 **Castiel Novak**

{picture of Castiel}

Castiel Novak, lead actor on the hit show Mishapocalypse, is no stranger to this list, he has been frequenting it ever since he made his debut as an established actor. His sudden rise in fame shocked many people, but what shocked people more is that he has been single for most of his life, and he mentions he has no intention of rushing into any kind of relationship. This not only makes him one of the most popular and respectable, but one of the most difficult bachelors to get with, so if anyone was planning on trying to get him, you better have a good plan to make him fall head over heels. Here is what was said:

 **Interviewer:** Do you see yourself getting in a relationship anytime soon, and what is the reason to not wanting to be with anyone right now?

 **Castiel:** No, I don't see myself getting into a relationship at this moment in time. I have found it difficult to find anyone who I would like to be with because everyone I have ever tried to be with only liked me for my fame or because they loved Misha, the character I play. But it isn't that I don't want to be with someone, it would be nice to have someone like that in my life. It just isn't the right time for me yet.

Click Here to Continue Reading

XXXXX

The days pass and finally the time Dean and Sam, along with many other people, have been eagerly awaiting for comes along. As soon as Dean got home from work Thursday, he sprinted up the steps to his room and is now throwing his clothes into a duffle bag haphazardly in an effort to be done more quickly so they can leave pronto. Although he should know Sam is taking his sweet old time and is going to have to wait for him to finish packing before they can leave anyway, but that doesn't matter, he is too excited.

Once all his things are packed and ready to go, Dean leaves his room and practically hops down the steps, shouting over his shoulder to his brother as he runs and grabs the tickets. "Hurry it up, Sam! The Winchester express is going to be on route in five!"

Sam rolls his eyes and lugs his bag out of his room bringing it down to the Impala where his brother currently threw his bag in. "I don't know why you're so excited, it isn't like the convention is today. All we're doing is going to the hotel."

"You can't tell me you aren't excited, Sammy. It's tomorrow! You get to meet Jess Saturday." Dean smacks his brother's shoulder and goes over to the driver's side door and hops in, hands tapping the steering wheel to the nonexistent music. Sam can't help but crack a smile seeing Dean this happy. It's been a long time since he has acted like this, and he isn't going to ruin his mood.

Dean is always worrying about Sam or how he is going to pay the bill, and the smile on Dean's face during those times is so strained, there is nothing happy about them. Dean only forces the smile because he doesn't want Sam to know they are having a hard time right now. All the teachers at Dean's school are. So yes, seeing a genuine smile on his brother's face is enough to make Sam feel giddy and like a kid in a candy shop. His brother is everything to him, and he wishes that Dean would stop worrying so much about him and worry more about himself. But there is no stopping Dean when it comes to putting Sam first, Sam knows this and he's given up trying to stop him.

Dean constantly worrying over Sam and putting, pretty much everyone, before himself is one of the many reasons why Sam wants Dean to find somebody to get into a relationship with. So the person he's with can watch over Dean and pull him back when things get out of hand and maybe smack a little sense into him because he doesn't listen to Sam when it comes to that kind of stuff.

Dean has never been good at taking care of himself, and if Dean had someone other than Sam to help Dean would do him good — because frankly, Sam isn't around Dean enough to take care of him the way he wants to. But Dean hasn't been in a serious relationship with anyone since Lisa about four years ago, he claims he doesn't want to get into another long-term relationship and he is happy now, but Sam knows that isn't true. Sam just wants Dean to be happy, and if Sam has no other choice he will play cupid again.

Sam's got his work cut out for him, that's for certain.


	3. Chapter 3: Elevators Are Good Luck

I was planning on writing all three days in one chapter, but it was slowly becoming waaay too long xD so I cut it in half. Plus side, you get a new chapter earlier than I was originally planning. Down side, ?  
Also, as for the convention itself I kind of skip a lot of it because reasons. I hope you enjoy this chapter and I apologize for the late update. I would blame college, but that would be a lie … I just kept procrastinating, but it's done now!  
I also want to thank everyone who reviwed, favorited, and followed. It means a lot!

* * *

 **Chapter 3: Elevators Are Good Luck**

Dean's alarm barely gets out half a scream before he is slamming a hand on it and sliding his finger across his phone's screen to silence it. As soon as he does this, he kicks his legs free from the blankets wrapped snuggly around them and springs from the bed. Typically Dean is not a morning person, but today it's like he's a completely new person, he feels so rejuvenated and excited. Today is the day. Today is the first day of the Mishapocalypse convention.

Dean practically prances to the shower. "Rise and shine, Sammy!" Sam groans in his bed and repositions himself to get more comfortable, mumbling something about shutting off the sun. Dean laughs and heads into the bathroom knowing Sam will get up in a bit. Sam is usually the morning person, but that's only after he is up and awake.

While in the shower, Dean's mind keeps trying to imagine what the convention is going to be like. He's never been to anything like this before. The only thing he has been to was a concert he didn't even enjoy, and he is assuming it isn't going to be like a concert so he has no idea what to expect. Although the main event about this convention is supposed to be something called a panel and they have seats for that, though it is first come first serve for general admissions seating, so maybe it is similar to a concert.

While finishing his shower up, he pushes his thoughts aside and starts to hum along to a song playing in his head. When he gets out and gets dressed, he leaves the steamy bathroom toweling off his hair; cool air hitting him as he step out of the door. He's ready for the day, but when he looks at his brother he has barely gotten up. The only indication that he is, in fact, awake is that his eyes are open.

"Did you fall asleep with your eyes open or are you dead?" Dean throws the towel over the back of the chair at the desk and when there is only a small grunt from his brother, Dean turns back around and waves a hand over his eyes. "Earth to Sammy, should I start digging a grave?"

Sam rolls his eyes and pushes Dean's hand down, sitting up. "I'm awake. I was just waiting for you to get out of the shower."

"Oh good you're showering, you were really starting to get ripe."

"I showered yesterday, Dean." Sam sighs running a hand through his hair as he makes his way to the shower. "Give me ten minutes and I'll be ready."

"Alright, I'll be down at the breakfast buffet."

Sam nods and Dean grabs his things for the day and leaves the room, ready for some food in his stomach. When Dean gets out of the elevator and to the buffet, he grabs a plate and fills it with enough food to last him until lunch. He sets his plate on a table, along with his bag with their stuff in it, and goes back to get a cup of coffee. Just as he sits down and is about to start eating, he hears a voice that he wasn't expecting to hear.

"Dean-o, I had no idea you were staying in the same hotel as me. What a little coincidence this is." Gabriel walks over to Dean's table and points to the chair in front of him. "Do you mind?" But he puts his plate of food down and sits before Dean can have a chance to answer. Gabriel then grabs his fork and shovels some food into this mouth. "So what brings you here today? Assuming you aren't here for the convention because you said you weren't going to it. But what is the coincidence that you are staying at a hotel this weekend in the area of the convention." Gabriel blows some air out of his mouth to signify what a weird coincidence it is.

Dean rolls his eyes at Gabriel because Gabriel obviously knows why Dean is here. "You can cut the act, Gabriel. You know why I'm here."

Gabriel smirks. "I know, I just wanted to hear you admit it." Gabriel takes in some more food, swallowing before he speaks. "So you're here alone?"

Dean swallows the food in his mouth shaking his head. "No, I'm here with my brother."

"Ohh, little Samerella, how's he been? Haven't seen him in a while."

"He's fine, this is his birthday present. He wanted to meet Jess again so I decided this would be the way to do it."

A look of realization crosses Gabriel's face. "Wait, you weren't the one who wanted to meet Jessica? It was for Sam?"

Dean nods. "Don't get me wrong, I'd love to meet Jess, but damn those tickets are fucking expensive."

Gabriel arches a brow. "What ticket do you have?"

"Normal admissions. Like I said, as much as I would kill to have a better ticket, this day is for Sam. I'm fine with sticking back so he can have more fun."

Before Gabriel has time to say anything, Sam walks up to them with a surprised look on his face. "Gabriel, you're staying at this hotel?"

Gabriel beams a smile at Sam. "Samerella, nice to see you again."

Sam rolls his eyes leaving to go get food. "I lose my shoe _one_ time." Dean and Gabriel both laugh, and when Sam gets back he sits beside them.

"So, Sam," Gabriel starts with a smirk on his lips. "I hear you get to meet Jessica."

Sam's eyes widen and snap to Dean, who is chewing a large amount of food. Dean meets his eyes and sees the accusation in them. "Hey," Dean says through a mouthful of food. "I didn't say anything about your little cr... whatever." Dean cuts himself off before he can finish the word crush, but Sam narrows his eyes at him anyway because there is no way Gabriel hasn't pieced it together now.

"Whoa, whoa, you have a crush on Jessica?" Gabriel teases playfully.

Sam groans and rolls his eyes to Gabriel. "It was a long time ago."

Gabriel arches a brow. "She only just started acting though. How did you know her?"

Dean smirks pointing his fork at Gabriel. "Sammy here went to school with her."

Gabriel's eyes widen and he looks at Sam, and Sam nods. "It was back in middle school. We were best friends, but we lost touch because her parents moved and I didn't have a phone back then to get her number."

"He was broken up about it for weeks." Dean adds and Sam kicks his shin under the table. Dean scrunches his brows together mouthing 'ow' to his brother.

"Whoa, wait, so _you're_ the Sam she was talking about?"

Sam and Dean's eyes both widen and they take a moment to look at each other before looking back to Gabriel. "She talks about me?"

Gabriel sets his fork down on his empty plate and leans back in his chair. "Oh yeah, whenever she talks about her childhood she mentions you."

Sam whispers to himself, trying to let it sink in, "She remembers me."

Gabriel smirks standing up grabbing his plate. "Indeed she does, but I'm afraid I have to go. I'm being summoned. I'll be seeing you two later."

Sam and Dean both say their goodbyes to Gabriel, and when they're alone, Sam looks to Dean still in shock. "I don't know what I'm going to say to her anymore."

Dean furrows his brows confused to how that little piece of information that Jess still remembers him has made it so Sam doesn't have anything to say to her anymore. It should have had the opposite effect. "Okay, you're going to have to explain. I'm confused."

"I was going to tell her who I was and how I knew her, but now everything I planned…"

"Knowing she remembers you should give you more to say now. You can spend your time trying to woo her."

Sam narrows his eyes at Dean. "I'm not going to have that much time with her, Dean."

"Okay, and that's why you have to work fast." Dean stares into his eyes and sees the nerves building up. Dean nods setting his silverware down. "Okay, here," Dean pats the table with his hands and turns his body to face his brother. "Practice what you're going to say to Jess on me."

"What? Dean, no way."

"I can give you pointers. I'm trying to help so you don't flub this up." Dean's face is completely serious, he wants Sam to be able to look back on his day and smile, not cringe and want to hide under his bed. "Now pull up your big boy panties and lock it in. I'm Jess, look at me with my beautiful flowing blonde hair and dazzling eyes." Dean pretends to throw a strand of hair over his shoulder and bats his eyes at his brother.

Sam rolls his eyes, but clears his throat and prepares himself. "Hey … Jess, uh," He clears his throat again, not looking Dean in the eyes. "I don't know if you recognize me."

"Stop." Dean interrupts making Sam look at him confused. "You can't be looking at the floor while talking to her. Look her in the eyes and show her how confident you are." Dean points at his eyes then at Sam's, telling him to keep eye contact. "Again."

Sam sighs running a hand through his hair. "Dean, this is never going to wo-"

"Again."

Sam hesitates for a moment, looking Dean in the eyes and seeing how serious he is about this. Pulling himself together, he gives it one more shot. "Hey Jess, I don't know if you recognize me, but we used to go to middle school together. I'm Sam Winchester."

"Oh my gosh, Sam?" Dean smiles widely at his brother as he plays the part of Jess. "It's been so long! It's so good to see you again. Oh, here, let me sign that for you." Dean smiles at him and takes Sam's napkin, pretending it's the thing Sam wants her to sign. Dean pulls out a sharpie from the bag at his feet and writes on the napkin, sliding it back to Sam when he's done.

Sam looks down at the napkin and sees Dean's little message. _'Text me if you're free later XXX-XXX-XXXX 3_ ' Sam looks back up and Dean winks at him. Sam scoffs. "Okay, you play a girl too well."

Dean pushes his imaginary hair over his shoulder with a triumphant smirk. "It's a talent."

"How do you know she is going to give me her number though. We haven't talked since middle school.

Dean points the sharpie at him. "That is precisely why she is going to give you her number." Dean leans back in his chair, hanging an arm over the back of it. "Follow what we just practiced right there and you'll be golden." Dean scoffs. "I don't know why you were so nervous, you did fine besides the eye contact thing. You just wanted to see me act like a girl."

Sam rolls his eyes. "Yes, because I was just dying to see you embarrass yourself in public because you don't do that enough on your own."

Dean and Sam eventually finish up their breakfast and when they do, the both of them head over to where the convention is being held to wait in line. They are in line for only ten minutes when the doors open and start letting everyone in.

The atmosphere alone is enough to put a smile on Dean's face. Thousands of people wandering around with the same interests and same reasons of being there as the brothers. There is an irreplaceable feeling of unification that Dean begins to feel, and he has only just got here. There are booths set up with merchandise for the show, there's a large screen playing episodes of Mishapocalypse, and there are people dressed up in cosplay of their favorite characters. Even with so many people being here he feels welcomed and very comfortable. It's like nobody is here to judge him.

"Why haven't we done this sooner?" Dean says and Sam huffs a laugh, still looking around excited. "What do you say we go look at the booths first before taking a seat for the panels. We have an hour before they start."

"Sounds good to me."

As the two of them walk around they see all kinds of t-shirts, sweatpants, hats, necklaces, rings, posters, etc. that they both really want to buy, and Dean would buy them all if he could, but unfortunately, they have twenty bucks each to spend. And as much as Dean really would love to buy something, he isn't going to because that twenty dollars could be used elsewhere, perhaps like buying food or going towards rent.

Adult responsibilities suck.

After about a half an hour passes of them just going around the booths and perusing the items, they go in the room where the panel is going to be held and find their seats. They are kind of far from the stage, but even from here they will be able to see them fine with that large screen on the stage. Sam could have sat up in the silver section, but he insisted that he wasn't going to leave Dean back here, and it would be more fun together. Sam even went as far as to find someone that has general admission ticket that came alone and told her that she could have his seat in the silver section. Needless to say, she was beyond thrilled and hugged Sam like her life depended on it, she even took a picture with him claiming she never wanted to forget him.

As the two are sitting in their seats, and people are slowly trickling in, Dean spots movement from up on the stage, so his eyes dart to it. On the stage is Gabriel walking quickly across it trying to get to the other side. He glances out to the chairs for a quick second then turns back forward, but then he stops and does a double take. He squints his eyes and stops walking, and when he knows for sure it's Dean and Sam he waves enthusiastically at them before strolling behind stage again.

Gabriel makes his way back behind-stage to find his brother, who had asked him to bring the, on the verge of passing out, stage crew member some water. He finds them and Castiel is kneeling beside her as she sits in the chair with her eyes closed tight.

"Here's the water."

Castiel's head turns back to his brother and he holds out a hand for the bottle, when he gets it he uncaps it and hands it to the women. "Here, drink this."

She grabs the bottle with a small smile. "Thank you."

Castiel smiles saying, "Of course." and stands up, leaving her in the paramedic's hands and walks off with Gabriel right behind him.

"Hey-o, Cassie, guess who I just saw in the crowd." Gabriel smiles walking beside Castiel. Castiel looks to his brother trying to figure out who was in the crowd. That's when Gabriel continues talking. "Yup, that's right. Dean is here," Castiel rolls his eyes knowing exactly where this is going. If it were anyone else telling him then Castiel wouldn't think anything of it other than being a little happy, but Gabriel never has good intentions. "But don't get too excited," He continues, "He is only general admissions. Although there is something you can get excited over." Gabriel wiggles his eyebrows at his brother who only has narrowed, unamused eyes on him. "He was only excited that Jessica is going to be here because his brother wants to meet her again. It wasn't for him."

"Gabriel," Castiel sighs scrunching his brows together. He doesn't want him to meddle like this, trying to get him to like Dean or vice versa. Castiel doesn't want Gabriel to get Dean into something that he can't get out of. Dean or himself for that matter. Castiel doesn't want to get his hopes up about Dean because, yes, he does, in fact, have a little crush on the man, and he is trying his damndest to veto those feelings back into the abyss of which they came. Although it appears Gabriel has other plans for Castiel and his feelings.

Why is Gabriel trying so hard to get Castiel to go out with Dean? Why Dean? Sure he seems nice and all, but why? Castiel loves his brother, but sometimes he wishes that he would leave his romantic life alone. No, scratch that. He always wishes he would leave his romantic life alone.

"Please leave Dean alone. The farthest I would like our relationship to go is friendship."

Gabriel, as if he didn't hear a word that came out of his brother's mouth, says, "You know he's staying at my hotel." This catches Castiel's attention and he looks back to him with a look of shock. Gabriel nods with an understanding expression. "I was shocked too. Neat little co-inky-dink if you ask me."

XXXXX

The panel for Friday only has the smaller actors from the show talking to them, but that isn't a bad thing. Dean enjoyed the panel, listening to people asking them questions and the actors answering them, sometimes with pretty hilarious stories. Sam had gotten up a few time to try and get some picture of the actors and actresses with his camera, that was far too expensive for Dean's liking, but he did end up getting some great pictures with it. Honestly, Sam's photography is so good Dean thinks he should just do that as a job instead of a lawyer, but Sam insists his pictures aren't good enough for it to be a profession. The time flew by so fast, Dean was shocked when it was the end of the first day.

Dean is now laying on his bed in his and Sam's hotel room, staring at the ceiling content. Sam is resting on his own bed, back against the wall and laptop sitting on his lap, fingers typing away at its keys. Dean rolls over on his side and stares at his little brother, waiting for him to notice. When he does, Sam furrows his brows at him in confusion.

"What?"

"Why don't we go out to eat?" Dean says with his cheek resting in the palm of his hand.

Sam thins his lips, pulling his bottom lip in between his teeth. "I would love to, Dean, but I'm on a roll with this paper and I think I can finish it tonight."

"We are on a vacation and you still only think about school. Typical Sammy for ya." Dean rolls back onto his back and gets up, heading over to the door and putting on his leather jacket. "I'll go grab us some food then while you torture yourself over that paper."

"Don't make it anything heavy."

Dean makes a disgusted face at his brother and shakes his head. "You and your rabbit food, I'm telling you."

"Dean," Sam sighs.

"Right, right, one bowl of lettuce coming right up Roger Rabbit." Dean smiles leaving their room. Just as Dean leaves the room his phone starts to vibrate in his butt pocket. He arches a brow and takes it out to look at the ID, but he wishes he didn't. Damn bill collectors, as if he didn't already know he is barely making his payments as is, they need to hound him for his money he doesn't currently have too.

Dean sighs stepping into the elevator and pressing the ground floor button. His face is contorted into that of frustration, but he can't help it, financial issues do that to him. Should he go out and get food? He is already so low as is. But he can't do that to Sam. Dean groans running a hand down his face and the elevator stops at the second floor to let someone on, and he runs his hand from his face to the back of his neck opening his eyes to meet familiar blue ones. His eyes widen in that moment realizing who it is.

"Cas." Dean immediately drops his stressed demeanor seeing Castiel look at him a little worriedly. He smiles a bit sheepishly then he realizes he just called him Cas instead of Castiel and maybe that look Castiel is giving him is confusion rather than worry. "Oh, I- sorry I didn't mean to call you Cas. It just felt … It just slipped."

A smile cracks Castiel's face and the elevator closes, taking them to the ground floor. "It's quite alright. I like the name." His smile drops and he looks as if he wants to say something. "Are you alright, Dean? You looked, pardon me if this is overstepping, but you appeared to be awfully stressed."

Dean chuckles a bit trying to play it off as if it were nothing when in reality it is his and Sam's life in his hands. "It's nothing, just been a long time since I've done something like this so it's kind of exhausting at the end of the day."

Castiel stares at him trying to judge the truth of the words, but even if he caught the half lie, he wouldn't say anything. Dean and Castiel aren't close enough for that yet. Instead, Castiel turns his attention to the opening elevator doors with a nod. "I understand. I get pretty worn out after these conventions too."

"Yeah, man," Dean laughs shaking his head. "I don't know how you do it. I have a whole new respect for you and everyone else."

Castiel smiles looking over to the blonde as they both walk out of the elevator. The small smile that is on his lips looks nice there, but there is a tiredness to his eyes that is unsettling to Castiel, he just can't put his finger on what it is about them. It is almost as if Dean is upset over something and is trying to suppress it, but before Castiel can think further on the subject, Dean interrupts his thoughts.

"So, I didn't know this was the hotel the actors are staying at." Dean looks around with some confusion. "I mean, it isn't terrible, but,"

"Oh, I'm not staying here. My brother is."

Dean meets Castiel's blue eyes realizing he was most likely just visiting Gabriel, so he mouths 'oh' and nods. "I forgot he's staying here too." Dean thins his lips trying to think of something to say. He wants to keep talking to Cas, but maybe he's tired and is heading back to go to sleep now. "So I'm guessing you're heading back to your hotel now?"

Castiel nods. "I am, but I'm going to stop somewhere to get something to eat first. I haven't been able to eat for a while."

Dean lights up, probably too much, but he can't bring himself to care. "Really? I was actually just heading out to grab my brother and me some food too."

"Oh? Where are you planning on going?" Castiel looks rather intrigued and surprised by the coincidence.

"Uh," Dean ponders trying to think of a store, but he honestly isn't sure. "I don't know yet. I just need to find a place that sells salads."

Castiel tilts his head to the side a bit, eyes squinted slightly. "You like salads?"

Dean scoffs. "No, it's for my brother." Dean grins and folds his arms proudly over his chest. "I'm an all meat kind of guy."

Castiel's eyes widen for a spilt second before he goes back to normal. "I know of a good place that sell salads and burgers. I was heading there myself, it is on the way to my hotel, if you would like to join me."

Dean's world spins for a second realizing Castiel Novak just asked him to join him to a restaurant. As friends of course. Although are they close enough to be called friends, or are they more of growing acquaintances? Either way, Dean is all for spending more time with Cas.

Dean shrugs, shoving his hands in his pockets trying to be nonchalant, and trying to not let his inner fanboy come out in public. "Yeah, I'll come with you."

A small smile appears on Castiel's lips and his eyes crinkle at the sides. That smile is lethal to Dean's health and he has to look away, but he can't. Castiel and Dean's eyes are locked and he can't tear them away. He can't help it; the smile in Castiel's eyes is captivating.

Eventually, Dean is the first to be able to break the gaze. He clears his throat and drops his eyes to the ground for a second before looking back into Castiel's eyes for a second longer and nodding towards the door. "Shall we?"

Castiel's eyes widen as if he had completely forgotten what they had been talking about. "Oh, yes. It's about a five minute walk from here, is that okay?"

Dean nods starting to leave. "Not a problem." Anything to get moving and to keep Dean's thoughts elsewhere.

While walking to the little restaurant — if you can call it that; it's more of a healthier fast food restaurant — Dean and Cas talked casually with one another about mundane things, work, laundry, cooking, everyday life things. In this conversation, Dean learns something that he doesn't know why he never thought of as plausible before. Actors are just like everyone else, and if Dean were being honest it makes him like Cas even more because of it. It makes him think that maybe, just maybe Cas isn't outside Dean's reach.

When Dean realizes what he's thinking, he quickly adds 'to be friends' to the end of his previous thought. A scowl then etches into his face because he can't fool himself like that, but he can sure as hell try. Thinking of a man like that … it isn't normal, so sue him for trying to correct himself. He isn't a lost cause yet, he can still turn himself around. His eyes turn to the dark haired man making his heart skip a beat and the scowl softens.

This is going to be harder than he thinks.

Cas meets Dean's eyes and points to the building in front of them. "This is it."

Dean tears his eyes from Cas' blue stare and looks up. It's a nice little place, and the outside is decorated pleasantly. It looks much nicer than any fast food place Dean has ever seen. He reaches forward and opens the door stepping aside motioning for Cas to go in. Cas nods his thanks with a small smile, and once he's in Dean follows behind. The inside is just as nice as the exterior, it's a nice change if you ask Dean.

"Do you know what you're going to get?" Dean asks looking at the slightly older man from the corner of his eye.

Cas thins his lips in thought, but he soon nods casting a glance to Dean. "Yes, I'm going to get a bacon cheeseburger."

Dean's eyes light up and he can't help but smile. "You like bacon?"

Cas arches a brow at him as if it's the most obvious question in the world. "Of course."

Dean nods approvingly crossing his arms over his chest. "It's official, we're now best friends. There is no getting rid of me now, you've dug yourself a hole that there is no escaping from."

An amused glint raises in Cas' eyes, and he stares at Dean's profile for a few seconds longer than intended before turning his attention to the menu again. "What about you, do you know what you want?"

"I'm gonna get the bacon cheeseburger too, but the question is, what do I get for Sam and his rabbit food?" He sees Cas' lips twitch into a smile at the mention of rabbit food, and Dean feels his confidence get a little boost. See, it's funny. Sam just doesn't appreciate his humor, but Cas does, and that is honestly one of the best feelings he's had in a while.

"I've gotten their caesar salad before and thought it was pretty good, perhaps he would like that."

Dean shrugs. "Sure, I'll go with that."

Cas lets Dean order first, and once they've both ordered and paid they sit at a table together and wait for the food to be done.

"Man," Dean starts, catching Cas' attention. "I don't know how you do it."

Cas furrows his brows with a squint and tilts his head to the side. It is one of the most adorable expressions Dean has ever seen and he can't get over it. "What do you mean?"

Dean motions to the clock. "You always have to eat this late?"

"Not all the time, just during conventions. Sunday, the day I have my panel, is the latest I get to eat, but I don't mind it. I just have to eat a little later lunch and I'll be fine."

Dean scoffs leaning back in his chair, "If I had to do a panel, and my panel was late at night, I would bring food on stage and eat it while answering their questions. If I'm hungry I'm gonna eat, screw being socially acceptable."

The corner of Cas' lips twitch up in amusement. "I don't know how well that would go over with management."

"Pfft." Dean waves a hand as if it's nothing. "I have my ways of sneaking food into places without getting caught. They'd have a hell of a time trying to stop me. Though I could never be an actor like you are, so I'll never get my chance to piss off the system."

"Have you ever tried?"

Dean arches a brow locking eyes with him. "Tried what? Acting?"

"Yes."

"Oh, no way. That's not a glass of wine I'm going to try anytime soon."

"You don't think you would be any good at it?"

Dean shrugs looking away. "It's not that I don't think I would be good, I'm great at acting when it comes to lying about things." He almost sheepishly meets focused blue eyes. "I probably shouldn't say that like it's something to be proud of, but it's true. The reason why I don't want to try acting though, I don't want to expose Sam." Cas' features soften in complete understanding. "If I tried it, and I got famous, people would try and learn everything about me, and there are some things I'd rather not have dug up about me. Although I couldn't care less about me and my privacy; my main concern is them finding Sam and taking away his privacy."

"I understand," Cas says, eyes never leaving Dean's for a second, but before he can finish what he was planning on saying, their numbers are called. Dean huffs in frustration, not wanting to leave yet, but he and Cas get up and grab their food, the both of them walking back outside.

Dean looks to his right, where he has to go to get back to the hotel, then back to Cas' eyes. They appear dark because it's night outside, but Dean is still able to see some blue because of the nearby streetlamp. "Well," Dean sighs rubbing the back of his neck. "Looks like this is where we part ways."

"Yes," Cas says hesitantly.

"I, uh … I hope I'll get to see you again," Dean says a little hopeful.

"I hope so too, this was fun for such a short endeavor," Cas smiles, making Dean crack a grin too. "But I'm sure I will see you, if not tomorrow, then Sunday at my panel. If you are staying of course."

"Oh, you better believe I'm staying." Dean laughs.

"Then I will see you Sunday, have a good night, Dean."

"You too, Cas." They linger for a few seconds longer, neither wanting to be the one to break the eye contact, but Dean eventually turns with a wave and leaves. Once he's further away, he spares a glance back to see Cas as a little figure in the distance under a light. After that, he heads straight back to the room.

When he closes the door to their hotel room behind him he throws the salad at his brother and plops himself on his own bed. Sam looks over to Dean, then to his salad, but he has to do a double take seeing the smile, not only in Dean's eyes but spread all over his face. Not to mention he's practically ebbing happiness.

"Something good happen?"

Dean snaps himself out of his thoughts, trying to wipe the smile from himself, but he only half succeeds. He turns his eyes to his brother, who is staring at him curiously. "Why do you think something's up?"

Sam gives him a bitch face, not buying into his little act. "You're practically beaming, Dean. Either something great happened, or you're scheming something awful." Sam pauses for a moment. "And if that's the case then I want to know what it is so I can get the hell out of dodge."

Dean rolls his eyes at his brother and takes a bite of his burger. "I just ran into Cas in the elevator, I wasn't sure where to get some food so he showed me this little fast food place." Dean shrugs as if it was some kind of everyday happening, but in reality, he's still reeling over the occurrence.

Sam is quiet for a moment longer than Dean would like, so Dean looks over to him. The look of shock is written all over his face, but there is also confusion. "Cas is staying in this hotel?"

"No, he was visiting Gabriel."

"Oh," Sam says quietly while looking at his salad. "I'm really wishing I went with you now."

Dean smirks taking a large bite of his burger, not bothering to swallow before he starts talking. "I tried to bring you along. You have nobody to blame but yourself."

Sam scowls at him before taking a grumpy bite of salad, muttering, "Jerk."

"Bitch."


	4. Chapter 4: For The Love of Trivia

A chapter update on time?! xD I was really feeling this chapter and couldn't stop writing it and because of that it's like ... really long. Also meaning I could have missed spelling errors and whatnot, but I tried to catch them

As for Sam and Jess, I wasn't planning on going more in depth with their relationship. I was just planning on talking about it every now and again, but if any of you really want me to add them into the story more and actually have moments from their POV I can do that

Other than that, I hope you enjoy! AND thank you to everyone who commented, kudos, and bookmarked! Don't be afraid to tell me what you thought of this chapter \\(^-^)/ I don't bite

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 **Chapter 4:** **For The Love of Trivia**

The next morning Sam woke up earlier than Dean, he was nervous all night and he wasn't able to sleep well at all. Today is the day he gets to meet Jessica again after all. Today will make or break him. If he screws this up, he will never forgive himself.

But no pressure.

Dean wasn't surprised to see Sam already up and around by the time he woke up. If Dean were in his brother's shoes he wouldn't have slept at all, honestly, he'd be a mess on the inside and barely holding it together on the outside. And Dean being Dean would find a way to fuck it all up, but Sam isn't Dean, he's better than him. He won't mess this up, he's going to be just fine. Dean is sure of it.

After Dean finally got around, and the both of them ate, and by both it means mainly Dean because Sam didn't want to hurl his breakfast all over Jess if he got too nervous, they went to wait in line.

When they are finally inside, Dean slaps his brother on the back with a wide grin. "Knock 'em dead cowboy. I'll be waiting here when you're done."

Sam stumbles forward a bit from the hit, but he catches himself before he can fall flat on his face and bust up his nose. Straightening himself out he gives a small nod. "Alright."

Dean frowns and grabs his shoulder looking at his brother, who is staring at the meet and greet line for Jessica. "It's gonna be fine, Sam. Just remember what we practiced."

Sam turns his eyes to his brother's green ones and sees the honesty in his words. He really believes Sam can do this. That makes one of them at least. It may seem silly to some people that he's getting so nervous, but this is absolutely terrifying to him. What if she doesn't like who he's become?

Dean sees the fear and panic starting to rise in his brother's eyes, so he squeezes his shoulder to bring his focus back to Dean and away from his thoughts. Overthinking situations is always the way people deter themselves. "Stop working yourself up. Remember, she is still Jessica, she's still human and not any different than you and me. She is going to be _thrilled_ to see you."

Sam looks away, still nervous. "But what if she's disappointed in who I am now?"

Dean is dumbfounded. Sam is worried about _that_? "What is there to be disappointed about?"

Sam turns his attention back to his brother, slightly shocked at how genuine the words sounded. Sam was expecting Dean to make a lighthearted joke to lighten up the mood and tell him not to worry. What Sam wasn't expecting was Dean genuinely asking what there is to be disappointed about because he can't think of any possibility that there's anything to be disappointed over.

"Sam, of all the things you could worry about, her being _disappointed_ in you is not one of them. Believe me."

Sam turns his eyes back to the line with a newfound determination. "Thank you, Dean." And he starts to walk over to the line, a smile growing on Dean's lips watching his brother.

Sam waits patiently in the line for his turn, trying not to over think anything. Honestly he's trying not to think at all. Thinking will lead to doubt and doubt is very bad. When it finally comes to be his turn, he is clinging to Dean's words like a lifeline to keep his shit together. He walks up to the table with a smile and hands her the picture he would like her to sign. She looks even more beautiful in person, and he starts to get nervous when she smiles widely at him as if he was every other fan that has come up to her today. Because to her, he is just like every other fan.

"Hello," She cheerily greets, uncapping her marker. "What's your name?"

"I'm Sam."

A light chuckle escapes past her lips as she signs her name. "I used to have a good friend named Sam." She looks up into his eyes.

Sam's heart is hammering against his ribcage. It's now or never. "I, uh … I know." She furrows her brows clearly confused. "I'm guessing you don't recognize me, but we used to go to middle school together. I'm-"

"Sam…" She gasps and her eyes widen. "Oh my god, Sam?"

Sam smiles sheepishly. "Hey, Jess." All of a sudden Jess pulls the large man around the table and jumps at him with a huge hug. Sam takes a moment to catch up with what's happening, and when he does, he wraps his arms around her tightly before letting go.

"It's been so long! It's so good to see you again, I can't believe it's really you." She keeps a hand on his bicep, staring into his eyes. Her smile is so bright it could blind someone, it isn't like that smile from when he walked up, this one is just for him.

Sam chuckles and rubs the back of his neck. "Yeah, same goes for you. I had no idea you were going to be an actress. I thought you wanted to study law."

She shrugs and drops her hand. "That's a long story." She sees her manager motioning for her to wrap it up and she sighs with a small smile looking back to Sam. "I'm getting yelled at to hurry up."

Sam's eyes widen. "Oh, I'm sorry, yeah, let's take the picture."

Once their picture is over Sam goes to grab the picture he had Jess sign from the table, but she stops him by putting a hand on his arm.

"Hold on, can I write something on that before you take it?"

"Oh, sure." Sam takes his hand off it and Jess slides it towards herself writing something on it before sliding it back to Sam with a smile.

Sam looks down at the picture and sees Jess' little message:

 _'Text me later XXX-XXX-XXXX 3_

 _~Jessica M.'_

Sam huffs a little laugh at how accurate Dean's little act was, but he doesn't need to tell Dean about it and boost his already inflated ego. Sam smiles up at her and Jess waves a little goodbye as he leaves.

Out where Dean is waiting for Sam, he finally sees his brother emerge from the crowd and Dean excitedly stands from his seat and claps his hands together approaching Sam. "How'd it go? You kill it in there? Of course you did, you didn't come out crying. Way to go, Sammy!" Dean wraps an arm around Sam's neck and pulls him down to mess up his hair.

"Dean! Knock it off!" Sam swats at Dean trying to get him to let go. Dean only laughs, but decides to let him go. When free, Sam desperately tries to fix his hair with an annoyed glare at his brother.

"So?" Dean says expectantly.

"What?"

"Don't 'what?' me, Sammy. I need to know how it went! I've been waiting out here, agonizing over it. Let me hear it."

Sam scoffs and slowly smiles. "It went good, Dean."

Dean throws his hands in the air. "That's my Sammy! I always believed in you."

Sam laughs shaking his head. "I know you did."

The rest of the day goes by quickly. Dean and Sam are near the back again during the panel, but today is Jess' panel, so Sam was up and running around with his fancy camera trying to get pictures of her, all while trying not to be in anyone's way. But he's 6'4 and running around like an energetic overgrown puppy, so he's bound to get in some people's way, though not for long. Before long it's the end of the second day.

XXXXX

And before they know it, it's the last day of the Mishapocalypse convention, running to try and make it in time for the trivia game. Sam is practically dragging his brother. Last night when he was texting Jess, she accidentally let it slip that the special prize that comes along with the trivia game is a dinner with Castiel, and Sam is going to get Dean into that game if it's the last thing he does.

"Sam, why are we running? So we're a little late, I told you I can't play anyway, I'm normal admissions, and you don't want to play it!" Dean shouts so Sam can hear him.

"And I told you that you are going to play in that damn game!" Sam yells back.

"Why do-" Dean stumbles and quickly catches himself, "Why do you want me to play that badly?!"

"Because I care deeply about your wellbeing!"

"That makes absolutely no sense!"

"Shut up and run, Dean!"

Dean knows that the winner of the game gets 500 dollars and some special prize, but still. Sam much really want Dean to win that money. He's not going to lie, it would definitely help them out quite a bit.

The brothers burst through the door and run up the table where the man was taking contestants for the trivia game, only to see he's closing up. Sam huffs a breath trying to calm down from the absolutely hectic morning. Sam will be damned if he can't get Dean into that trivia game. It's the least he can do for his brother for everything Dean has done for him so far. If it weren't for Dean, Sam never would have gotten Jess' number, or at least not this soon. Also, Sam did not just drag his brother's ass out of bed in record time to take no for an answer.

"My brother would like to join the trivia game, please. I know we're a little late, but please." Sam practically begs sliding his own silver ticket to the man. The man looks down at the ticket and sighs for a second before scribbling 'CONTESTANT' on it in big letters.

"It starts in two minutes. You better hurry."

Sam takes it eagerly and shoves it into Dean's hands. "Thank you! Thank you so much." He then grabs Dean and speed walks to the stage because running is prohibited as he found out yesterday when he and Dean got too excited over something and security yelled at them. When they get to the stage the security man that yelled at them yesterday is standing there, he looks at them and Sam points to Dean. "He's a contestant."

Sam looks back to Dean and nods towards the guard to show him the ticket. Dean holds out the paper and the guard looks at it then nods stepping aside to let Dean pass. Dean stumbles up onto the stage and when he catches himself, he straightens up and slowly looks out to the crowd. His throat constricts for a second, but he tries his best to look confident. That's a lot of people out there. Honestly, Dean has no idea how this all happened since his brain hasn't caught up with Sam's abnormally fast pace this morning, but he's just going to roll with it.

Back behind stage Castiel is waiting patiently for the game to begin, but when he looks out from behind a curtain and his eyes widen. Dean is being ushered on to the stage by a guard. Someone else by the stairs, he can only assume that person is Sam, is giving him a thumbs up and telling Dean to 'kick some ass'. A small smile cracks Cas' lips at that.

As Dean stumbles onto the stage and quickly collects himself, head turning to the crowd and hesitating for a second. And in that second, Cas can see the nerves building up in Dean. It makes Cas want to walk out there and try to comfort him and tell him that it's going to be fine, but he can't. It would draw too much attention to the man if Cas singled him out like that, and Dean said he didn't want anything like that. So Cas restrains himself, telling himself Dean will be fine.

"Oh, no way, Dean-o's playing?"

Cas glances back to his brother who is holding the microphone ready to head out on stage. Cas turns his attention back to the contestants. "Yes, he just got here it seems." Cas hesitates for a moment, but if he doesn't say something then he is going to be worrying the whole game. "Gabriel,"

"Yes, dear brother of mine?"

Cas meets his eyes. "Can you try and not draw any attention to Dean. Act as if you don't know him."

Gabriel scrunches his brows together. "Why? Doesn't that seem rude?"

"Dean told me on Friday that he doesn't want to be famous, and I know you acting like you two are good friends won't make him famous, but it will put a possible target on his back that he doesn't want. So please act as if he is just another contestant."

Gabriel stares into Cas' eyes for a moment before a smile cracks his face. "Not a problem."

Back on stage, Dean is quickly seated beside a blonde woman and is momentarily blinded by the lights shining on them. He squints and blinks repeatedly to get adjusted to the new situation. Soon the guard comes back with two papers each numbered one to five and a pen. Dean takes it and nods his thanks. He takes a look around and is feeling suddenly out of place. Everyone, besides two others, are women. There are only three men out of twenty contestants.

All of a sudden someone walks out on stage holding a microphone, and Dean has to do a double take when he sees it's Gabriel. Gabriel makes eye contact with Dean and raises his brows suggestively, but only Dean saw it. Dean arches a brow and looks around to see if that really was meant for him, and if it was, then what did it mean?

"Hello, everyone large and small and everyone in between. I'm Gabriel, as many of you probably know," The crowd cheers loudly cutting him off for a moment, and he waits for it to die down before continuing. "And I am going to be your host for this year's game of trivia." The crowd whoops and hollers, and Gabriel being Gabriel, takes a bow, and he smiles widely at them bringing the mic back up to his face. "Thank you, thank you, you're all too kind. But really, you shouldn't." The crowd starts to die down and Gabriel has a look of fake offense written all of him. "I didn't say you could stop cheering." He motions for them to start back up again and when they do his smile spreads wide. "Alright, alright, enough about me and how awesome I am. How about we give it up for the contestants!" Gabriel turns to them and starts to clap and the crowd ignites again.

"It's time to go over the rules! Whoo! Okay, so you all have two pieces of paper numbered one to five on each. There are going to be two rounds to this game, each with five questions. If you miss one question in the first round then you're out, if you make it to the second round and then end up missing one in that round, you're out and cannot play the final round. I know, this is difficult, but this prize is for the super fan. Oh, and as for the special prize you win, it's dinner with your very own, Castiel Novak." The crowd erupts, and even the contestants on stage lose their cool. Dean, on the other hand, doesn't know if he wants to win now.

Why? Because if he answers all the questions correctly then he is going to look like an obsessive freak stalker. Will Cas think of him differently? Will Cas think Dean only cares about being with the lead actor of his favorite show? But he really wants to see Cas again, not to mention the 500 dollars would be great.

Gabriel grins wickedly at those on stage, eyes falling on Dean. When he sees his hesitation he arches a brow, but he doesn't have time to ponder what's going on in Dean's noggin right now. He looks back to the other contestants smirking. "Remember, you're not here to make friends, you're here to win. Show no mercy." Gabriel pauses for a second thinking that over. "But no physical violence, please. Be gentle." The crowd laughs at that.

"Before we get started, I have to say it." He pauses. "No cheating, play fair or else it isn't any fun, but I know you're all amazing people and would never dream of doing something like that." He puts a hand up to his mouth as if to whisper to the contestant, but he brings the mic up too saying, "Especially not with so many eyes on you." The crowd laughs and he smiles clapping his hands together. "Now how about we get this show on the road?" Gabriel looks back to the contestants as the crowd cheers, he casts a glance to his little card with the questions on it. Once he's got the question, he smiles and scans over them. "Okay, we're going to start this one off real easy as a little warm up. Gotta stretch your mental legs. I need you to think long and hard on this." He pauses for dramatic effect. "What is Misha's last name?"

Once everyone finishes writing the answer Gabriel rolls his eyes. "What part of 'think long and hard' did you not understand? That took all of five seconds." He throws his hands in the air and walks over to the little podium, leaning on it and reading the next question. "Fine, since you are all just so smart, write down for question two, who was killed in the pilot episode? I want a name."

Gabriel smiles seeing someone already struggling, but she finally writes an answer. "Looks like I already stumped someone, but it's all good, don't worry, the next question is more difficult."

"Question three!" He holds up three fingers. "What character was only supposed to make a one-time appearance but ended up being on for four seasons?"

Dean leans back in his chair, arm thrown back over the backrest. These questions are easy so far. If they remain like this then he has this in the bag.

"Hopefully you all know your missions because if not then this next question is gonna be rough." Gabriel reads over the question once more. "What episode was Misha's first _official_ mission that he failed, I want the title of the episode, and why did he fail?"

Dean arches his brow in thought. Gabriel stressed the word official. That means … Dean's eyes widen and he quickly jots his answer down.

Once everyone is finished writing, Gabriel continues. "Okay, this is the last question for round one. I hope you've all seen the latest episode. In the most recent episode, who is Adrianne looking for in the end of the episode? Gimme the name."

Dean nearly scoffs at how easy that question is.

"Alright, I'm coming around and I'll check your answers. If you're out, please make your way off the stage and to your respective seats. I will go over the answers out loud after I finish this." Gabriel makes his way around the contestants and checks their answers. These questions were so easy, Dean was sure that not many people were going to be told to leave the stage. Dean wasn't expecting half of the contestants to be out in stage one that's for sure. When Gabriel gets to Dean, the last contestant, there are only about 11 people left, including him.

Gabriel looks over his paper and laughs, confusing Dean. Did he answer something wrong? "Great job." Gabriel chuckles as he turns away and heads back to the podium. Dean furrows his brows and looks at his paper. What was so funny?

"Alright, the answer to question one, his last name is Collins. Question two, Misha's wife, Sharlot was killed. Question three, Misha's therapist, Carter was only supposed to show up once. That one really got a lot of your guys. Question four, The failed mission episode was titled, Black and White. The reason behind his failure was because he wasn't able to kill the innocent children. Question five, Adrianne was looking for her brother, Dmitri." He looks back to the remaining contestants. "Congratulations to you 11, you made it to round two." He looks over them once more. "Are you ready?" They all nod and he smiles.

"Great, then we'll waste no time. Question one, In the episode "Thunderstruck", what did Matt tell Misha?"

Easy.

"Next question. Misha was adopted, does he know any of his blood relatives, if he does, who does he know?"

Dean stretches out his legs and scribbles his answer.

"Next. In what episode did Misha finally go to a therapist for what happened to Sharlot, and who convinced him to go?"

Dean probably shouldn't be so proud of how easy this is for him, but damn it's easy.

"Question four. Did, or does, Misha have any children?"

Dean purses his lips. That's a trick question, isn't it? Sharlot was pregnant when she was killed, but that doesn't mean they had the child yet.

"And finally, I'm not going to lie, this one is a tough one. There are two parts, and I will repeat this if anyone needs me to. Part one, finish the sentence. _'I will find them, and when do _.'_ " Gabriel pauses waiting for them to write their answer before continuing part one. " _'I don't care about _. I'm doing this so that _ will never be able to _.'_ " He pauses once again. " _'I will _ and I will not _.'_ " When he sees them all finish writing he says, "Do any of you need that repeated?" One of the women nod and Gabriel repeats the first part slowly.

Dean thinks the question over carefully in his head. He knows this line well. It was a turning point for Misha.

When Gabriel is done repeating the question he continues, "Alright, and part two, who was Misha talking to?"

Dean is hesitant about part one, but part two he knows he got right.

"Alright, I know that one was killer, and if nobody got it right then we'll do a different one, so don't stress out. I'm going to come around now and check your answers."

Gabriel makes his way around, and so far nobody got the last one correct all the way, but he hasn't told them to leave the stage just in case nobody gets it right and they have to do a different question. But when Gabriel gets to Dean, he looks over his answers and his eyes widen slightly looking rather impressed. Gabriel holds the mic behind his back so it won't catch his voice as he hands Dean back his paper.

"Damn, Dean-o, you must really want that dinner with my brother."

Dean glares at him. "Oh shut up, Gabriel. I was forced into this."

Gabriel smirks rolling his eyes. "Uh-huh, suuure you were." Gabriel turns back to the crowd and brings the mic to his mouth again. "I apologize to the other eight contestants, but it looks like we have a winner." The contestants leave the stage and Gabriel motions for Dean to stand. "What's your name, kiddo?"

Dean gives Gabriel a confused look. Gabriel is only three years older than Dean, what's with the nickname? Besides, Gabriel knows his name. Unless he's embarrassed to know Dean and is acting like he doesn't. If that's the case he doesn't want to make a scene, so he just answers. "Dean."

"Congrats on your win, Dean-o." Gabriel looks back to the crowd. "And thank you all for participating in our game. I'm going to go over the answers now. For question one, they found the gang who killed Sharlot. Question two, no, Misha doesn't know any blood relatives. Question three, The episode was called "Lullaby" and Matt was the one who convinced him. Question four, No Misha never had any children, but Sharlot was pregnant when she was killed. And lastly, question five, Misha was talking to Matt, and the complete speech is: _'I will find them, and when I do_ _I will kill them_ _. I don't care about_ _revenge_ _. I'm doing this so that_ _abomination_ _will never be able to_ _put anybody else through what I have_ _. I will_ _dedicate my life to stopping him_ _and I will not_ _rest until he I see the life drain from his eyes_ _.'_ That was one hell of a game, but I'm afraid it is time for me to leave. Have a great rest of con, try not to miss me too much!" He waves as he puts an arm around Dean leading him off stage, and he hands off the mic to the person going out on stage.

Dean wants to let it go, but he has to know if Gabriel is actually embarrassed to know him. "Were you acting like you didn't know me?"

Gabriel arches a brow and looks at Dean, lowering his arm and smiling. "Yeah, Cassie told me to. Said you didn't want to be famous or something, yadda, yadda, yadda, so I played along. Acting is in my blood after all."

Cas asked him to do it? Dean's eyes widen for a second. Is it because of what Dean said on Friday to Cas? He remembered that? And he even went to such lengths to make sure he didn't get too much of a spotlight on him.

Dammit, Cas, Dean is trying so damn hard to not have a damn crush on you. You can't go and do something like that!

Wait, Cas knew he was on stage, so that must mean he's-

"Hello, Dean." Cas' voice interrupts his thoughts, as if on queue.

Dean turns his head and looks into his eyes that Dean just can't get enough of. "Cas,"

Gabriel looks between them and smiles. "Aww, look at you two already flirting, but I'm afraid I'm going to have to ask you to save it for dinner."

Both Cas and Dean tear their eyes away from one another and glare at the brunette. Gabriel backs up holding his hands in the air. "Alright, I'll just go get the check for Dean-o here, you two can chit-chat till your heart's content."

Dean and Cas watch as Gabriel retreats, and when they're finally alone, or as alone as they can get at the moment because of stage crew running around, Dean looks to Cas a little nervously. "Were you watching that?"

Cas turns his head and meets Dean's gaze when he hears his voice. "Of course."

Dean licks his lips looks away, he doesn't know why he feels so nervous right now, but he does. Maybe it has to do with the fact that he got every answer right and Cas is probably thinking Dean is just some overgrown fanboy. "Well, now I look obsessed."

Cas has an amused smirk play across his face and light up his eyes. "Dean, what did you think was going to happen if you won?"

"I didn't think I was going to win, I was actually planning on purposely flubbing up just so I wouldn't because I didn't want people to think I'm pathetic. Hell, I wasn't even planning on playing until Sam practically threw me into it."

Cas frowns at the fact that Dean was going to purposely throw the win just so people wouldn't think he's pathetic. Why Dean would think anyone at a Mishapocalypse convention would think someone who loves the show is pathetic is beyond Cas. "Is that why you looked so confused when you got onstage?"

Dean scoffs lightly. "I wasn't mentally prepared for any of that."

"And yet you still won."

Dean pulls his bottom lip between his teeth, he isn't used to so many people knowing about his love for the show like this, he doesn't know how to react to it. "Okay, yes, I really like the show. I know a lot about it, but I'm not a stalker or anything. I just remember things easy."

Cas' frown doesn't leave his face, in fact, it deepens. "I never accused you of being such a thing. I think it's nice that you have something you're so passionate about, be it a tv show or anything else. Everyone has something they love to do in their spare time, or else life would be boring." Cas tilts his head a little, eyes squinting slightly. "You shouldn't be embarrassed about liking something, Dean. And as for people thinking of you as pathetic, nobody would do that. Especially not here."

Dean stares into his eyes for a moment before the whole situation begins to become too raw and emotional for him, and he has to look away from his piercing blue eyes. "Well to society, adults aren't supposed to be," he motions to all of him. "like this. They're supposed to be responsible and have socially acceptable interests or hobbies."

"Dean, from what I heard from Gabriel, you're very responsible. He told me about the papers you misplaced." Cas leans over to try and get Dean to look at him so he can see the truth in his eyes, but Dean doesn't meet his stare.

"Yeah, but someone who's responsible wouldn't have lost the papers in the first place." Dean sighs rubbing his neck. He doesn't know why he's talking about this and to Cas of all people. He should just let it go and act as if it's nothing. As if it doesn't bother him at all because it really shouldn't. Typically he doesn't care what people think of him, but when it comes to Cas or Sam, he can't stand the thought of them thinking badly of him.

"Accidents happen to anyone, Dean." Cas' eyes remain squinted as he tries to figure out what's eating away at Dean, but it appears Dean wants Cas to back off, so he will begrudgingly let it go. Even though he was to get through to Dean, but something tells Cas that now isn't the time. They barely even know each other.

Dean clears his throat feeling rather uncomfortable under such an intense stare. A part of him feels flattered that Cas seems to care so much, but the other part of him is telling him this is going too fast. Nobody has ever cared about him like this in such a short amount of time and it is making him nervous. But maybe that's just how Cas is, maybe he does this to everyone.

"Cas, what d-" But Dean doesn't get to finish what he was about to say before Gabriel comes back and interrupting Dean.

"I come bearing gifts." He waves an envelope bouncing up to the two, but his bouncing slows once he sees the tension between them. "Did I interrupt something? Y'know, don't answer that. I'm just gonna … back away."

"Yes," Cas says a little irritated.

"No," Dean says at the same time as Cas. They look to each other for a second and Dean is the first to look at Gabriel. "It's fine, Gabriel. I get to see him later anyway." Dean says with a smile. "I'm sure Sam is wondering if you kidnapped me, so I should probably get back to him now anyway."

Gabriel gives a mock hurt expression. "I would never."

"Uh-huh," Dean smirks taking the envelope Gabriel is offering him and looks to. "I'll see you later, Cas."

"Of course. Goodbye, Dean."

"Come backstage after Cas' panel, okay?" Gabriel adds quickly before Dean leaves.

Dean nods and waves his goodbye. When he leaves the stage he makes his way towards the back, and it doesn't take long for him to find his brother. Sometimes Dean likes Sam's height, it makes it hard to lose him in a crowd. Sam instantly stands up and makes his way over to his brother since there were no seats around him for Dean, and the both of them make their way towards the back.

"Dude, how did you remember that? I could only remember half of it." Is the first thing Sam says to his brother.

"All that school work is frying your brain, Sammy. It was easy." Dean says smugly.

Sam rolls his eyes and huffs a laugh. "Okay, sure. Nerd."

"Oh, I'm the nerd?" Dean says turning his head to Sam.

Sam smiles. "I never said I wasn't a nerd. I'm simply saying you're one too."

"I am not a nerd."

"Okay." Sam says holding up his hands in defense and once Dean looks away Sam adds, "You're a closet nerd."

"That's not even a thing." Dean glares.

"It is now."

"Shut up." Dean rolls his eyes.

Sam laughs but remains quiet for a little while, but his curiosity gets the better of him. "So, what did you do backstage?"

Dean casts a glance to his brother before looking back to the stage where one of the actresses is talking. "Gabriel just gave me the prize money and then told me where to meet up with Cas after his panel."

Sam nods but keeps his eyes on Dean, feeling there's something more but Dean isn't saying. "That's it?"

"Yeah. Don't wait up for me tonight, I have no idea how late I'm going to be out."

"Okay, I don't think I'll have a problem with that."

Dean arches a brow turning his head in Sam's direction. "What does that mean?"

"I'm going to dinner with Jess tonight."

Dean's eyes widen. "No way, really?" When Sam nods Dean beams a smile at him. "See, I told you she'd be thrilled to see you again." Dean scoffs looking back to the stage with a teasing roll of his eyes muttering, "Worried she wouldn't like you."

"Oh, shut up."

The teasing dies down between the brothers as the panels continue, and eventually, the time rolls around for Cas' panel. When he walks out on stage the crowd erupts. He turns a warm smile to the crowd and waves before he takes a seat on the lone chair in the center of the stage. Even from the distance that Dean is at, Cas still looks breathtaking. The panel begins with him talking a little bit, but then it quickly transitions to him answering fan questions.

Some of the questions are genuinely interesting, and others are funny. There were a couple questions about Misha's past and what Cas thought of it, which was rather interesting to hear what Cas thought about it. The one thing Dean was, sort of, expecting to happen, didn't. He thought at least one person would ask something about Cas' personal life, but nobody brought it up. It seems fans have more respect than he gave them credit for. Although, Cas does tell stories of his own accord when answering some questions, but that's different from a fan asking for something personal.

But perhaps Cas doesn't mind answering personal questions, maybe it's just Dean. Dean has never been someone who likes sharing a lot of information about himself if it's too personal, or if it's something that brings up something he'd rather keep buried. So he doesn't like talking about his feelings, or showing true emotion, so what?

Although because he does this, his brother calls him emotionally constipated, which got a chuckle out of Dean the first time he heard it.

Nearing the middle of the panel, Cas stood up and started to walk around. Dean guessed he was starting to get stiff, which is understandable. But then Cas started to walk down the aisle because, Dean didn't know why, maybe the stage wasn't cutting it for him, but the whole time he's walking around the aisle he continues to answer the questions. When Cas gets near the back of the room his eyes scan past Dean, but he pauses for a moment and looks back, making eye contact before smiling a little and continuing. He then looks at Sam with a little nod and turns.

Dean smirks and crosses his arms over his chest watching Cas look over all the other fans in the crowd, waving here and there. Sam, on the other hand, is, simply put, shook. Not because Cas made eye contact with him and acknowledged his existence, though that was pretty sweet, but because the look that he shared with his brother. It was only there for what seemed like a nanosecond, and if he wasn't looking at Cas with all his attention he never would have seen it, but it was there. What _'it'_ was though, Sam isn't sure, not exactly.

Yes, Dean met Cas before and that could have just been Cas' look of recognition, but something tells Sam that wasn't it. Plus, the look Dean has right now isn't something he has very often. Sam may not know Cas well enough to deduce a conclusion, but Sam is a Dean expert, and that look Dean has on right now. That's something he's only seen a few times. Granted this look is more guarded and it's giving Sam the 'emotionally constipated' vibe that Dean seems to exude, but it's still there.

This makes Sam's eyes widen slightly. Really he shouldn't be shocked, but Dean has never shown interest in men before. Although Sam shouldn't assume things. That only leads to false assumptions and could go very badly. He is going to need proof, and if Dean really is into men too, then Sam has a feeling Dean isn't even out to himself yet and is very confused. That leaves Sam with two decisions. Let Dean figure it out himself, which might take years of frustrated feeling and self-hate, or Sam can drop hints of accepting bisexuality and try to help Dean out.

What is he thinking? There is only one option or else Dean will never come out.

Plan "Help Dean Out Of The Closet" is a go.

XXXXX

After Cas' panel ended, Dean did as he was told by Gabriel and makes his way behind stage. He thankfully doesn't need to show the security guard any kind of identification since he knows Dean was the winner, and Cas or Gabe most likely told him just to be sure.

As Dean walks backstage he sees a bunch of people walking around cleaning things up and getting ready to leave. They're all probably excited or relieved that this was the last con this year for Mishapocalypse. Dean can only imagine how much work it takes to conduct and keep these things in working order, making sure there is no mass chaos.

Just as Dean is about to ask someone where Cas is, he hears him behind him. "Hello, Dean."

Dean turns around to see Cas smiling at him, meeting his stare. "Hey, Cas." Dean looks around before meeting his unwavering stare again. "So, where are we going on this little adventure?"

"Follow me." Cas turns and begins to walk, Dean quickly catching up and walking beside the man. When they get outside they go to the parking lot where there are the actor's trailers. Dean's heart skips a beat for a second seeing them. Are these the trailers they use for shooting the show, or are they personal trailers?

Cas turns to Dean and motions to his trailer, looking almost shy. "I hope you don't mind, but I had food brought to my trailer for us."

Dean's eyes widen at the realization that he is going to get to go inside Cas' trailer, but he calms himself down and gives Cas a playful smirk. "Are you inviting me into your trailer?" Dean is about to make a joke about moving fast, but the words get caught in his throat. Those words would physically hurt him coming out.

Cas' eyes widen and all of a sudden he starts to get a little panicked and starts to speak rushed. "I … I just thought it would be more private since you told me you don't like … you wouldn't want your privacy taken from you and the paparazzi can be ruthless if they saw us together. But we … we don't have to eat here, we can go-"

"Cas," Dean says feeling a little guilty he made the actor nervous. "Cas, you're rambling."

Cas snaps his mouth shut. "I'm sorry."

A soft smile plays at the corner of Dean's lips. "It's fine, Cas. I was only teasing, I'd love to eat dinner in your trailer." Dean chuckles a little as Cas' shoulders slump in relief. "You really go out of your way to make sure I never feel too exposed ever since I told you about that privacy thing."

Cas' expression becomes nervous again. "Is that bad?"

"Cas, relax." Dean laughs walking towards him a little so he can clap a hand on his shoulder. "It's a joke." Dean locks eyes with the dark haired man and he can't help himself, he wants to see his reaction. "If I didn't know any better I would say you're trying to keep me all to yourself." Dean winks and a light blush dusts across Cas' face causing Dean's heart rate to pick up slightly. He was not expecting this to backfire on him like this. Cas is cute when he blushes. Dean laughs patting Cas' shoulder. "Sorry, sorry, that joke went too far. I'll stop now."

Dean drops his hand from Cas and Cas watches him closely. When Dean turns his head away from Cas there was a look in his eyes that meant something was bothering Dean. Does Dean make jokes when he's in situations that make him uncomfortable? Cas frowns slightly and calms himself down.

"Are you sure you don't want to go out to eat?"

Dean quickly turns back to Cas with a worried expression. Had he really gone too far? Is Cas uncomfortable with this now? Has he already managed to fuck this all up? "No, no, really, Cas it's fine. It's more than fine. I really appreciate all that you did for this."

Their eyes lock and Cas searches for any unease in Dean, but he doesn't see any. Cas gives a small smile to try and lighten the mood. "Alright." And he walks over to the door opening it for Dean.

Dean walks into the trailer and he has to marvel at it for a second before he can continue. It's so much bigger on the inside than Dean ever would have imagined. Not to mention how well decorated it is. The door to the trailer closes and Cas comes up to stand beside Dean. Dean's eyes finally land on the food sitting on the table and he smiles. Damn, that looks good.

Cas sees his smile and part of him is relieved. "I wasn't sure what you would like to eat, but I remembered you told me you liked meat, so I thought steak would be a safe route."

"Hell, Cas, steak is the best route." Dean beams a wide grin at him before making his way over to the small table, Cas right behind him. They sit down across from each other and Dean can feel the warmth radiating off the food indicating he was just made not long ago.

"I hope it's to your liking," Cas says picking up a fork and knife.

"There's no doubt this is going to exceed all expectations." Dean grabs his utensils as well and cuts into the piece of meat, and when he takes a bite, the taste is beyond what he expected. By far the best steak he's ever had. He can't stop the quiet moan from escaping him as he savors the taste. He looks up and sees Cas a little shocked by Dean's moan and Dean laughs. "Sorry, It's just really fucking good."

Cas's expression lightens up and he cracks a smile. "I'm glad." As they continue to eat, Dean chuckles a little at the whole situation. Cas looks up confused.

"I never would have thought buying my brother tickets to meet Jess would ever lead to me having dinner in your trailer. Sorry, I…" Dean chuckles a little more. "It's just hard to believe." He looks up meeting Cas' eyes and sees the confusion in them. "What?"

"You were excited about Jessica because you're brother wanted to meet her, not you?"

"Yeah," Dean takes a bite of food. "Sam and Jess went to school together back in middle school and he's always had this major crush on her ever since."

Cas feels relief wash over him at this information, but also guilt because Gabriel had told him about it, but Cas didn't believe a word he said. Cas thought his brother was only trying to meddle in his life again. He will have to apologize to him later.

Cas pulls himself out of his thoughts before Dean starts to question why he's not answering him. "And your brothers got to meet her I assume?"

"Oh yeah, they're actually going to dinner tonight to catch up."

Cas smiles. "That's nice to hear."

The two of them continue to talk to one another, the conversation taking a few interesting twists and turns. Dean learns that this is, in fact, Cas' trailer he uses for everything. Dean also learns that Cas never watches movies and has only seen a few from when Gabriel forced him to watch them with him, Dean vowed to change that. But when the conversation turns to family, something Dean loves and hates to talk about at the same time, Cas becomes a little more serious.

"I envy you, Dean," Cas says, startling Dean a bit.

He scrunches his brows together, not understanding why anyone would ever envy him. "Why?"

"You have a normal life, and where it might not be easy, I really do envy it." He pauses for a moment, but he doesn't meet Dean's stare, and having finished their meals long ago he has nothing to occupy himself. "What you said before about not wanting to act because of privacy. I really do understand that." His eyes trail up Dean's chest and stop on his eyes. Dean is listening intently, not wanting to interrupt Cas. "As you probably know I was born into the world of celebrities and flashing lights. Paparazzi always on my doorstep. I was never given the choice to lead a normal life. Gabriel, he tries, but people still know him and will go to him because he is part of the Novak family." Cas' face faintly turns into a frown for a second before going back to normal. "I'm not saying a life like yours is easy by any means, especially since I don't know what you have been through or what you still go through, but I envy it. That's why I have been trying to keep your privacy safe, and I will try to do that because I would like to think of us as friends, and friends do that kind of thing for one another."

Dean's eyes widen and his mouth parts slightly as if he was going to say something but stops. Cas realizes what he said about being friends might now be something Dean would want and he tries to cover it up. "I-I … if you would like to be my friend that is. I'll understand if you would like to no because you want to protect your brother and you ar-"

"Cas," Dean cuts him off.

"Yes?" Cas says almost nervously.

"You're rambling." Dean cracks a smile and Cas slightly blushes. "Besides, I already told you we're best friends and there was no getting rid of me, didn't I?"

A small, relieved, smile appears on Cas' face. "Yes, you did."

Their eyes remain locked on each other's for what feels like minutes, but in reality it is only a few seconds before Dean break is. "Let me see your phone," and before Cas can look confused Dean explains. "I'm going to give you my number." Cas reaches into his pocket and pulls out his phone, handing it to the Winchester. Once they have each other's numbers the night slowly rolls to a close and Dean decides he should get back because he has work tomorrow.

"Are you sure you don't want me to walk you back?"

"Cas," Dean laughs. "It's a five minute walk. I'll be fine."

Cas frowns, clearly unhappy, but there isn't anything he can do to change Dean's mind. "Alright, then I hope you have a good right of your night."

Dean smiles back at him stepping out of the trailer. "You too, Cas."

"Goodnight, Dean."

"Night, Cas." Dean waves and begins to walk through the dark parking lot. Dean wasn't sure how this night was going to pan out before, but he sure as hell wasn't expecting to have such a deep conversation with Cas. Although he can't really say he's angry about it, not that he would be angry anyway. Cas seems like such a caring person, no wonder why everyone loves him on and off screen. Also, not to mention, Dean now has Cas' number programmed into his phone, and he couldn't feel more like a schoolgirl that just met her favorite idol.

Tonight was a good night.

XXXXX

 **Sam Winchester** S_Winchester

Had a great time at the #Mishapocalypse convention with my brother. I was able to get some great pictures too.

{pictures of Gabriel, Castiel, Jess, and Dean from up on stage playing trivia}


	5. Chapter 5: Team Emotional Laxative

Back with another chapter! Thank you all who have been reading this and favoriting, following ,and reviewing!

Just in case you wanted to see the pictures/read it on AO3, this is where you can find it (Just replace dot a period): **AO3 dot /works/12218790/chapters/27752979**

* * *

 **Chapter 5: Team Emotional Laxative**

Monday. God, Dean hates Monday. Especially the Monday after such an amazing weekend. Forced back into his reality, back to his everyday, boring, stressful life. Dean just wishes he could go back and relive it, to feel a little worry-free again. Talking with Cas like that, Dean felt so at ease during that dinner. Almost as if he had known Cas his whole life. And for that moment, he wasn't focused on his life and what he has to do to keep afloat. It felt good.

Alas, all good things come to an end. That's a motto Dean has come to live by.

The only thing that he likes about this Monday is talking to Charlie about the convention during lunch. Charlie immediately started interrogating him for answers the moment she stepped into the lounge. Although it wasn't really an interrogation since Dean took little to no coaxing to get the answers from him, which was a shock.

And yet again, after that, Monday was just the same old Monday Dean has come to love to hate.

When Tuesday rolls around, Dean has the new episode of Mishapocalypse to look forward to. He settles down on the couch next to his brother, dinner in hand, ready to watch the episode completely unaware of Sam's inconspicuous fidgeting.

Sam has been thinking about how he wants to bring up the whole sexuality thing to his brother. It sounded so easy at the time he thought of the whole 'Help Dean Out Of The Closet' idea, but actually going through with it is going to be a challenge. He'll wait until after the episode to bring it up though, use this time to try and think up a plan.

The episode of Mishapocalypse starts off with Misha as his new undercover persona. He's talking with some people, looking cool and collected. He reminds Dean of an Italian gang leader in that suit and slicked back hair. It's a good look on Cas. Not the Italian gang leader thing, the actual look he's wearing is kind of … enticing.

As the episode continues, it goes between Misha and Adrianne, but mainly focuses on Misha. There was even a moment that had Dean and Sam on edge because Misha and Adrianne accidentally bumped into one another in the street, but that was as far as that encounter went which was frustrating. It had Dean yelling at the tv for her to turn back around because Misha would be able to help her. Nearing the end of the episode is cuts to Adrianne again. She's on the computer typing away and trying to dig up information to find her brother. The screen slowly pans around from her back so they can see her face and it slowly closes in. Her brows knit together and all of a sudden her eyes widen and she mouths 'Oh my god' before she quickly stands, grabs her coat and keys and leaves her motel room. The screen turns back to her computer screen and it shows a picture of Misha, and that's when the screen goes black and the credits roll.

"Wait…" Dean says leaning forward suddenly connecting what they left hanging. "Misha is…"

"Dmitri?" Sam finishes his brother's thought and they look at each other wide eyed.

Dean snaps his eyes to the screen. "No way! How … what … when … how did she … Misha … I want to text Cas and ask him but I know he can't tell me…"

Sam looks him in the eye and shrugs wanting his brother to text Cas because reasons, so he encourages his thought even though Cas will most certainly not confirm it. "Doesn't hurt to try, does it?"

Dean makes a face of agreement and nods. "Yeah, you're right." He pulls out his phone and shoots Cas a quick text.

 **Dean: Are you telling me Misha's real name is Dmitri? Cas, Sam and I can't deal with this suspense. You gotta put us out of our misery, man…**

Dean sets his phone on his lap waiting for a response that comes a lot quicker than he or Sam, judging by his shocked expression by the vibrating phone, expected. Dean picks it up and reads what Cas said.

 **Castiel: I see you watched the new episode. I wish I could put you both out of your misery, but the most I can do is distract you by offering to send my brother over to you. He has a talent for never being quiet, I'm sure he could help. Although I understand you may not want him, neither do I right now, so how about I offer you something else to help take your mind off it?**

Dean can't help but laugh. Cas is a lot more open and joking in text than Dean imagined he would be. The grin doesn't leave his face as he types out a reply.

 **Dean:** **How thoughtful of you Cas. What is it you're gonna offer me? ;)**

Sam arches a brow growing ever curious at what they are talking about. "What'd he say?"

Dean looks up tapping his phone on his knee with a chuckle. "I think Gabriel is annoying the shit out of Cas right now. He offered to send Gabriel over here to make us stop thinking about the show, but then-" Dean's phone buzzes and he picks it up reading over the message slowly. "he said … that …" His voice trails off reading the last sentence.

 **Castiel: The producer told me that I was able to bring friends backstage in-between my scenes if I wanted to because I work so much. The only rule is the people I bring have to stay away from the area while the scene is being filmed. Would you and Sam like to come and see the set on Saturday?**

"…Holy shit…" Dean whispers to himself, but Sam is still able to hear it.

"What?" Dean looks up and simply hands him his phone so Sam can read Cas' message. When he's done he looks at Dean with wide eyes. "Dude you better say yes or I'm going to do it for you."

Dean scoffs a laugh, still in slight shock at what Cas asked. "Don't worry, there's no way I'm passing this up." Dean types out a response and reads it over a few times, not wanting it to come out as too boisterous, before sending it. One exclamation point will suffice, even though he wants to slam the button a hundred times.

 **Dean:** **Hell yeah, Sam and I will be there!**

 **Castiel: Great, I will text you the details (:**

Dean can't help himself. That smiley face Cas sent….

 **Dean:** **Cas, your smiley face is backwards…**

 **Castiel: I don't see a problem with my smiley face, Dean (:**

 **Dean: Cas … don't do this …**

 **Castiel: Don't do what, Dean? (:**

 **Dean: Cas…**

 **Castiel: Okay, I'll stop**

There is a pause in the texts, then,

 **Castiel: Is this better? (o:**

 **Dean: Oh my god Cas you're doing this on purpose…**

 **Castiel: (o:**

 **Dean: That's it. I'm gonna find you Cas. You have been warned.**

 **Castiel: Turn that frown upside down, Dean (o:**

 **Dean: I'm leaving to come find you now.**

 **Castiel: I look forward to seeing you.**

Dean rolls his eyes. Who knew Cas could act just like Sam sometimes?

 **Castiel: Have a good rest of your night, Dean :)**

Dean doesn't even try to stop the smile from forming on his face. That little shit.

 **Dean: You too, Cas.**

Sam watches his brother as he talks to Cas, and for a second he thinks that maybe this might not be so hard. Sam pulls out his phone acting as if he just get a text from a friend. Time to put his plan into action. He unlocks his phone and goes into his texts and gives his best fake surprised face.

Dean smiles up from his phone and looks to his brother, about to say something but stops when he sees Sam's face. "Sam? Something up?"

Sam gives a quick sturgeon face before shrugging lightly. "Nothing really, just my friend. She just texted me she's a lesbian."

Dean gives a small smirk, not able to resist teasing his little brother. "You have friends, Sammy?"

Sam turns his famous bitch face to Dean, who holds his hands up in defense with a laugh. "Dean, this is big for her. This is big for anyone who comes out."

Dean lets out a sigh running a hand through his hair as he leans back on the couch. "I know, I'm sorry."

Sam thins his lips studying his brother's reaction before Sam drops his eyes back to his phone. "I'm not really surprised or anything though, she's been acting like she's into girls for a while now, but it's still a big deal to finally admit to it. I just want her to know that it's okay."

Dean arches a brow at Sam's weird behavior, but ignores it and holds up his beer for a second. "Hey, maybe you can introduce her to Charlie." Dean winks at Sam and Sam just rolls his eyes. Dean raises his brows looking innocent. "What, too soon?"

Sam lets out a disgruntled sigh running a hand through his hair. This is going to be harder than he thought, and as much as he doesn't want to exploit his brother's possible secret, he's going to need an expert. Scrolling through his contacts he clicks one and types out a message, re-reading it a few times and making sure this is the right thing to do before he decides that yes, this is the right thing and he hits send.

 **Sam: Charlie, I need your help. Can you meet me tomorrow at Gabe's Café after work? Also, don't tell Dean.**

XXXXX

Sam is sitting at a table by a window in Gabe's Café waiting for Charlie to get off work. He looks out the window and sees Charlie look in and give him a big smile, in which he smiles back. When she comes into the small café she quickly orders herself a coffee and sits across from Sam.

"So, Sam, what's with the top-secret mission vibe you're giving off right now?" She smiles and leans in whispering, "Do we need to hide a body?"

Sam chuckles at her and shakes his head. He's missed, Charlie. "No, nothing like that."

She nods and leans back. "If it isn't a body, why wasn't I allowed to tell Dean?"

Sam presses his lips into a thin line and sighs. "Because it's about Dean."

This instantly catches all of her attention. "Did he do something?"

"No. It's just … I know-" He rubs the back of his neck trying to find the right words. "You came out years ago so you know how to help someone who is still in the closet, right?"

Her eyes widen. "Sam, are you trying to come out to your brother?" Sam's eyes widen. "You don't have anything to worry about, Dean will be completely fine with it!" She smiles warmly. "He had no problem with me."

"That's not it, Charlie…"

She furrows her brows running the conversation over in her head once more before realizing what Sam's saying. "Dean?"

Sam nods. "This is everything I know," Sam explains everything he's picked up from Dean and how he thinks his brother might be into Cas. He tells her that he tried to drop hints that it's okay to come out, but Dean didn't seem to pick up what Sam was putting down. That's when he texted Charlie, not wanting to keep failing and drag this out longer than needed.

Charlie bites her bottom lip and nods. "I thought there was something else behind his fascination with Castiel. He was elated on Monday when he was relaying the details of the convention to me." She meets Sam's eyes. "You did the right thing contacting me. Dean can be stubborn and you're going to need all the help you can get." She leans in a little and her voice turns to a whisper. "And from what you told me about your attempt to help Dean, maybe he wasn't picking up what you were saying because he doesn't know that he's into men too."

Sam wouldn't put it past Dean to be in denial to himself. "But if that's the case, then how to do we help him admit he's bisexual to himself? If we accuse him of it then he'll close off and knowing Dean he'll probably never admit it."

"And if we don't help Dean then he'll never admit it either." Charlie and Sam both sigh at this.

Then all of a sudden Gabriel waltzes over, grabbing one of the empty chairs at their table and sits down with a wide smile, his head resting in his hands. "Do, what's the top-secret mission you're discussing? Whatever it is, I want in."

"Gabriel, what…" Sam starts but cuts himself off to give Charlie a slightly nervous look. What did he hear? "I, uhm…"

"If you wanna know what I heard, I only know something about you two trying to help Dean." Gabriel meets Sam's concerned eyes. "I could be of some use, and I'm Dean's friends too so if he's in some kind of trouble,"

Sam thins his lips and drops his eyes to his coffee. "He's not necessarily in trouble." He looks up into Charlie's eyes trying to see what she thinks.

She shrugs and glances to Gabriel, then back to Sam. "He is his brother."

Gabriel's brow arches hearing that. He thought they were talking about Dean. "We're talking about Cassie?"

Sam shakes his head. "Not exactly. We're still talking about Dean." Sam gives Charlie a little look telling her not to give Dean's feelings away and she gives him an apologetic stare. Sam sighs rubbing the back of his neck. He feels as though he's exposing his brother's deepest darkest secrets that he most likely doesn't even know he has by doing this, but maybe Charlie is right. Gabriel might be able to help. Sam grumbles to himself for what he's about to do and he meets Gabriel's stare. "Anything you're about to hear from us is strictly meant to stay between us. If you agree to this then I'll let you help."

"My lips are sealed." Gabriel pretends to zip his mouth and lock it with a key.

Sam slowly nods. "What do you know about gay people accepting themselves?"

"I had to go through it a bit with Castiel, but his experience was easier than most." Gabriel shrugs.

"Wait," Sam's brows come together. "Cas is…?" Sam didn't want to say gay because he could be bi or something else, but Charlie finishes his sentence for him.

"Gay?"

"No, no. Not entirely anyway, he's …" Gabriel sighs clearly not knowing how to explain. Maybe he is trying to cover up for his slip because Cas doesn't want to come out yet. Although Gabriel said it was easy for Cas to come out. "Okay, don't tell him I told you this, I love him to pieces, but I just don't know how else to explain this. He's basically bi?" Gabriel rubs his chin in thought. "Or maybe Pansexual is the right term." Gabriel waves a hand dismissing it. "That's beside the point. He's, I'm gonna go with, pansexual."

Charlie worries at her nails as she listens to Gabriel talk, something not sitting right with her. "Is it okay for you to be telling us this? It seems Castiel doesn't want people to know."

"Oh, no it's fine, he's cool with it." Gabriel quickly reassures her. "I just said not to tell him that I told you he's pansexual because he doesn't like to identify with a specific sexuality, but that makes it really difficult to explain for some people, so for simplicities sake, I associated it with that. But he's not 'in the closet' or whatever. I can assure you he's very comfortable with his sexuality." Gabriel purses his lips. "Although I suppose I could have just said he doesn't specify." He shrugs shaking his head. "I'll get it eventually." He arches a brow at them, switching gears. "But what about Dean?"

Sam taps his fingertips on the wooden table leaning back in the hard chair. "I don't know for sure, but I think he's bi."

Sam looked over to Gabriel who is nodding lightly. "And?

"He's emotionally constipated," Charlie speaks up quickly, wanting to say it ever since she heard Sam say it while he explained what was going on. Sam gives her a smile knowing she's been itching to say it.

Gabriel nods again. "Meaning he either doesn't know it himself yet, or he does and is trying to ignore it?"

"Exactly." Sam sighs knowing that even with these two it's going to be difficult. "My brother, he's had a rough life, and I just want him to be comfortable with who he is. He was fine with himself for the most part when we were younger, but one day when he was 16 he randomly changed. I remember it like it was yesterday. The complete 360 of his personality." Images of that night flash in his mind and it gives him a little chill. "It was like he wasn't Dean anymore. Back then he was still figuring out who he was, like all of us, and looking back I see the same things happening again. I have a feeling if I don't help him with this then he's going to get frustrated with himself and never accept his feelings because they 'aren't normal', and the same thing is going to happen like when he was 16."

Sam runs a hand through his hair. He doesn't want Dean to go through that again. To this day Sam still has no idea what flipped Dean's switch, but he has an idea. Sam thinks Dean might have actually been with a guy and John found out. That's the only reason Sam can think of that would have such an impact on his brother. Dean is strong, but when it comes to John, he's like a terrified puppy.

Sam pulls himself from his thoughts to continue what he was saying. "The only way I can think of showing him it's okay is me trying to drop hints of it. I haven't had much experience with things like this though, so I called Charlie."

"Okay," Gabriel says mulling over what Sam has just said. "What makes you think he's into guys now?"

"I've noticed a certain look in his eyes when he's looking at a man, but it's guarded. As if he's trying to fight it off and dent it."

"So you think maybe he knows he likes men, but is just being bullheaded?" Gabriel inquires.

"That sounds like Dean." Charlie smiles.

"Then we could each just tell him about how it's okay." Gabriel shrugs. "Subtly, of course."

Sam shakes his head. "We can't all just start bombarding him with 'being gay is okay' things because he will catch on and know we're up to something."

"We are up to something," Gabriel smirks and it earns a smile from Charlie.

"We have to be careful about it though. Dean can be a bit touchy when it comes to his feeling. Being emotionally constipated is a task, on all of us. With him, we can't just ask him if he's bi/pan/questioning or whatever it is he is. We have to kind of … nudge him and show him it's okay, but not all at the same time or within the same time period."

Gabriel thins his lips a little concerned. "Is he cool with people being gay?"

"Oh yeah." Charlie beams. "Dean and I are best friends and I'm a lesbian, hell he even flirted with a guy for me because I had no idea how." Sam and Gabe both look to Charlie with an are-you-kidding-me look. Her eyes widen looking between the two. "What?"

"When did this happen?" Sam asks genuinely curious because he's never heard this before.

"Back when he got kicked out of the bar a few years back. He was trying to get me my laptop back from the bartender, remember?"

Sam furrows his brows confused. Gabriel rolls his eyes at her. "And you never stopped to question that maybe Dean was anything other than straight?"

Charlie pauses for a moment, just now putting the pieces completely together. "No, but now looking back I really should have. I just thought that since he's a guy that he would know what guys like to hear."

"Why did Dean get kicked out of a bar?" Sam asks still a little hung up on never hearing about this.

Charlie arches a brow and looks at him. "He never told you about it?"

"No, he didn't."

"Uh-oh," Gabriel teases. "I smell trouble in paradise."

Charlie laughs, albeit a bit nervously. "It was a long time ago. Long story short though, the bartender confiscated my laptop for … reasons and Dean tried getting it back. Some things happened and some words were exchanged resulting in Dean getting literally thrown out. He talked to me through an earpiece and told me what to say and I got my laptop back." Charlie thins her lips a little nervous. "Alright, back to Dean."

Gabriel smiles, amused at the story, but decides to help her out from Sam's interrogations. "Okay, but what I'm not getting is, if Dean is fine and dandy with other people being anything other than straight, why is it not okay for him?"

Sam frowns, his attention falling from Charlie back to the situation at hand and he leans back in his chair. "Our dad, he …" Sam pauses not knowing how to word it correctly. "He isn't one of the most … understanding people you'll meet. And when it comes to homosexuality, well, let's just say he doesn't like it."

Charlie frowns wanting to grab Sam's hand, but stop herself. "I never knew that."

Sam laughs a little, but it isn't from humor, it has a bitter aftertaste. "That doesn't surprise me. Dean doesn't talk much about our father, our dad was especially rough on him."

"So he has daddy issues?" Gabriel asks.

Charlie snaps her eyes to Gabriel in shock. "Gabriel…"

Gabriel looks at her for a second. "I didn't mean it disrespectfully, I'm just trying to get the picture here."

Sam laughs bitterly. "No, it's fine. You aren't wrong, not really. And I think if we want to help Dean accept himself, then I'm going to have to work with him about our father. He barely even listens to me when it comes to him, so this is going to be tough."

"Do you think…" Charlie starts but drifts off. She worries her bottom lip between her teeth before continuing. "Do you think Your father has to do with Dean's change when he was 16?"

Sam meets her sad eyes with his own. "Honestly? Yes."

Her hands grabbing her mug tightly getting upset thinking about what Dean had probably been through. "Has he ever thought about therapy? Having someone unbiased to talk to?"

Sam scoffs hearing the word therapy. "Dean would never dream of doing something like that." Sam twists his mug just to fidget with something and keep his mind in line. "It isn't like he thinks people that do go to therapy are weak, it just … he gets into his own head sometimes, you know? And with our dad … He made Dean feel that men who show emotions are weak."

"But he encourages you to not bottle up your emotions," Charlie says with a confused frown.

"He doesn't care if other people show their emotions, he does encourage them even, but he grew up always having to be strong and stoic. I think maybe he doesn't know how to show deep-seated emotions."

Gabriel leans back in his chair. He had no idea Dean had so much going on. Like Sam said he's only ever showed surface emotions, but Gabriel still considers Dean a good friend and he wants to help him. Although Castiel has always been the better one at helping people with emotions and talking about their problems. Gabriel thinks it's the soft look he gives people telling them it's okay and he's there to listen. No matter how hard Gabriel tries, he can never copy that comforting air about his brother. Therefore he comes to his conclusion.

"What if we bring someone else into this, someone that was like him once?" Gabriel looks to Charlie. "I'm not saying you weren't like him once, but maybe he's got into his head like you said, Sam. What if he thinks it's more difficult for men to come out and accept themselves in that way?"

Sam really hopes he isn't going to say Cas, but he has a feeling that's where he's going. "Who were you planning on asking to help?"

"Castiel."

Sam thins his lips and looks to Charlie who is giving him another slightly concerned look. Dean might not open up to Cas because Sam is pretty damn sure Dean has and has had for a while now, a crush on the actor. But that also might work in their favor. Because Dean has a crush on him, maybe he'll feel a little more connected and open up? But knowing Dean, probably not. Dean will probably close off about his emotions and not want Castiel to dislike him or think he's too broken and weird.

Gabriel arches a brow looking between Charlie and Sam. "What's with the secret eye conversation?" Gabriel's eyes widen realizing what is going on. "No way…"

Sam shoots a look at Gabriel. "Don't tell anyone." He whispers harshly.

"Even I wouldn't stoop that low."

Gabriel has to admit though, he does want to tell Castiel about Dean liking him. Cas wants Dean to fell for him so desperately, Gabriel can see it in his eyes, but Cas would never believe him even though it's the truth. Although getting into a relationship wouldn't be the best for Dean right now, and the relationship would be very fragile since Dean still doesn't know his he likes men. So the plan? Get Dean to accept his non-straight thoughts, then get Cas to admit he likes Dean, then get them together.

"To make Dean not the only one so exposed right now," Gabriel starts, looking into Sam's eyes. "I'm pretty sure, and when I say pretty sure I mean like 99.9% sure Castiel has a thing for Dean."

Sam and Charlie's eyes both widen and stare at the brunette. Sam is the first to break out of it and find his voice again. "Wait, really?" Gabriel nods and Sam huffs a laugh looking away. "Then that look he gave Dean at the convention makes so much more sense."

Gabriel leans on the table with his elbows looking rather interested. "He gave him a look?"

"Yeah, he smiled when he met Dean's eyes and it just made him look … relaxed."

"Right," Gabriel nods leaning back. "Okay, if we're doing this, we are going to need a team name. I vote Tem Emotional Laxative." Sam can't help but huff a small laugh and Charlie grins widely. "I take that as we're all in favor. Team Emotional Laxative is a go! Death to emotional constipation!"

A few people turn to look at them after Gabriel said that a little louder than he probably should have. Sam gives an apologetic look to them and looks back to Gabriel. "Okay, not so loud, Gabriel. You're going to draw attention."

Gabriel arches a brow at Sam and looks back to see the people staring, so he smiles and gives them a wave. When he looks back he taps his fingers on the tabletop. "So is it cool if I bring Castiel into this?"

Sam runs the thought over in his head for a second. Dean and Cas seemed to be getting along when Dean was texting him last night. Maybe Dean will open up to him more. "If Cas is uncomfortable with the idea, then he doesn't have to do it, so don't pressure him or anything, but if he wants to help then it's okay with me."

"Great," Gabriel claps his hands against the table, standing up with a smile. "You two talk out a plan, I, unfortunately, have to get back to work. Fill me in with the deets later." Sam nods to him while he turns away and leaves the two alone again.

Charlie looks to Sam a little worried. "You don't think Dean is going to be upset about this, do you?"

"Oh, he'll be more than upset if he finds out." Sam gives her a small, reassuring smile. "So we just have to make damn sure he doesn't find out."

XXXXX

Gabriel smiles at Castiel's slightly surprised look that's on his face after he just told him everything about their plan. Castiel sighs and runs a hand down his face, not really knowing what to say. He's shocked Dean is questioning his sexuality, and he knows Sam, Gabriel, and Charlie only want to help, but he doesn't really know if what they're planning on doing is right.

Castiel didn't really have a say in hearing what Gabriel had to tell him. He just came into his home and asked if Castiel wanted to help Dean. Castiel, of course, said he would help, but he thought it was a hypothetical question. Gabriel then proceeded to spill everything they had talked about. But Castiel knows Dean doesn't like his privacy being invaded without consent, and everything Gabriel just told him was very private. Castiel knows just how private and terrifying it can be to finally come to terms with sexual preferences, and if Dean isn't ready then he doesn't think they should try pushing him. Things like this take time. Although if he is truly miserable the way he is now like Sam says he is, then maybe giving a little nudge will be okay. Castiel feels a knot growing in his stomach.

What has Castiel gotten himself into?

"Gabriel, this feels like we are trying to put our noses where they don't belong. Dean doesn't like his privacy being invaded."

Gabriel smiles reassuringly. "It isn't invading privacy if we're just nudging him telling him it's okay."

Castiel's eyes narrow at his brother in slight agitation. "You have already made me invade his privacy by telling me he's sexually confused."

"In that case, it's too late. You might as well help us, or else you're going to be a bystander to a tragic life of emotional constipation and misery."

Castiel rolls his eyes looking away from his brother. "Sometimes you aggravate me, Gabriel."

Gabriel cracks a wide smile at his brother's irritation. "That's what brothers are for. Welcome to team E.L."

"E.L?" Castiel scrunches his brows.

"Emotional Laxative."

"Of course." Castiel rolls his eyes. "Tell me what it is you want me to do."

"Just, tell him you're into guys too. Give him a sales pitch, something like why only go after women when you can have both? The more the merrier, right?"

"Gabriel," Castiel says exasperatedly.

"Okay, okay, just casually bring up the conversation. Subtly bring up a past relationship you had with a guy. Easy enough, right?"

"Yes, I suppose." He sighs. "I still don't like this though."

"Yes, yes, complain about it later. So, when are you going to talk to him?"

"I already have plans with him and Sam on Saturday."

Gabriel furrows his brows. "You told me you couldn't do anything Saturday because you're filming."

"I am. Dean and Sam are coming to set."

"Oh," Gabriel smiles. "So you won't mind if I tag along, right?"

"It's not as if I can prohibit you. Security won't stop you."

Gabriel lights up at that and nods triumphantly.

Castiel frowns a little, not liking this at all. If Dean finds out that he is doing this behind his back, it could hurt their friendship pretty bad, and they just met. All he can do now is explain to Dean when he finds out because yes, Dean will most likely find out sooner or later. Castiel would tell Dean what they are doing, but from what Sam said, Dean is delicate about things like this and it could push him back.

And Castiel knows it's a crappy excuse to say he has to do it now because he could easily say no, but he doesn't want to see Dean upset or hurting in any way. So as much as Castiel doesn't like it, he's going to join in, but only as much as he has to.


	6. Chapter 6: On Set Experience

I finally finished it! Thank you all for the comments and the kudos! Finals week is coming up so I'm not sure when I'll get the next chapter written, but I'll try to get it done before too long.

Just in case you wanted to see the pictures/read it on AO3, this is where you can find it (Just replace dot a period): **AO3 dot /works/12218790/chapters/27752979**

* * *

Dean and Sam pull up to the set of Mishapocalypse that Saturday, both the brothers very giddy about getting to see the set of their favorite show. Cas had told Dean where to go and where he would be able to park, and thankfully Dean had no trouble finding it with Cas' directions. When Dean puts Baby in park, he grins over at his brother before looking out the rearview mirror to see the giant building that houses the stages.

"You ready to head over?" Dean asks and turns his green eyes back to his brother.

"I've been ready." Sam opens the door without hesitation and gets out, Dean following suit. Sam walks over to Dean and they begin to walk towards the number of warehouses. "Did he mention what warehouse it is?"

"Yeah," Dean points to the one right in front of them. "Warehouse 13."

"So the one with the big scary security guard."

"That's the one." Dean grins and strides up to the man. The guard gives him a once over with a sharp glare. "Hey," Dean says with a nod of his head. "I'm Dean, this is my little brother Sam Winchester. We're here for Cas."

The guards tough exterior loosens up a bit and he nods. "Yes, he told us about you both. I'll inform them, wait one minute." The guard pulls up the walkie-talkie hanging from his pocket and presses the button to talk into it. "The Winchester brothers are here."

After a second someone else's voice comes through the little machine. "On my way."

He puts the walkie-talkie back on his pocket and looks to the brothers. "He'll be here soon."

Dean thanks the guard and not a minute later the door swings open and Gabriel is standing there with a wide grin. "Dean-o, Samerella, glad you could make it. Cassie is in a shoot right now, come with me." He turns to the guard giving him a thumbs up. "Keep up the good work, Berry." Opening the door wider for the brothers, he motions for them to come in. "Follow me."

Dean and Sam both make their way into the warehouse, following Gabriel. Once inside, and their eyes are adjusted from the light outside, they look around and see people swarming every which way. People with headsets on, others holding clipboards and papers, people in suits, people in casual wear. It's organized chaos, and Dean is loving it.

"Since my baby bro is otherwise currently occupied, you two are stuck with me as your guide." Gabriel smiles back at them. And Sam is about to tell Gabriel that someone is coming towards them with a large prop, but Gabriel ducks without prompting from Sam. Gabriel jabs a thumb in the direction of the prop. "And be on alert at all time."

"How did you know that was there?" Sam asks rather questionably.

"Being here so often, one must acquire their sixth sense."

"You don't say." Dean mutters still looking around bright eyed and bushy tailed.

Gabriel takes them on a little tour of the place, mainly just showing them where the bathrooms are and where they can't go today because filming. Their last stop is the food.

Gabriel stops walking and turns to the brothers, motioning back behind him. "And this is where we get our food."

Dean perks up and his eyes dart to the buffet of delicious looking foods of all kinds. The aroma is almost too much and it has Dean's mouth watering.

Gabriel sees Dean eyeing up the food as if it's his prey and decides to put him out of his misery. "You going to stare at it all day or are you going to go get some before you start drooling all over my shoes?"

Dean doesn't need to be prompted any further before he's at the table with a paper plate in hand. Sam huffs a laugh at how eager Dean is about his food. That man is like an endless pit. While Dean is occupied with the thought of food, Sam uses this time to talk to Gabriel about Team E.L.

His eyes still locked on Dean, he asks, "Did you talk to Cas?" Sam says this a little quieter than probably necessary, but it's better safe than sorry.

"Sure did," Gabriel nods crossing his arms over his chest.

Sam arches an expectant brow in his direction. "And?"

"Oh, right, he was a bit skeptical about the whole hiding it an going behind Dean's back, and the whole lying aspect of it. Also, he didn't like the invasion of privacy thing because Dean mentioned to Castiel that he likes his privacy." Gabriel wracks his brain for everything else that Cas said before continuing. "He made it very clear to stress the fact that he absolutely hates everything about our plan, but he's in."

Sam scrunches his brows together, opens his mouth as if to speak, then closing it again only to give Gabriel a thoroughly perplexed look. "You did tell him he didn't have to join, right?"

"Of course,"

Sam narrows his eyes knowing there is a 'but' coming. "But?"

"But I may have accidentally pressured him into it by saying he has a choice, but also basically saying that if he did nothing while knowing everything I told him that he was going to be a life of tragedy and emotional constipation."

Sam sighs running a hand down his face. "So you guilted him into it."

"Basically, yes."

"Gabriel," Sam lets out a frustrated groan. "I told you not to do that."

"Yes, yes, I know, I'll apologize to him later."

Before Sam has the chance to say something back, Dean comes striding back over to them with a plate piled high with food, a smile spread across his face as he chews some food.

Sam looks down at his plate and shakes his head looking back up. "Dude, how are you even hungry after that lunch you had before we got here?"

Dean looks to his brother still contentedly chewing. "Free food, Sammy. My stomach knows no bounds."

Sam huffs a laugh. "I can see that."

Not long after Dean got the food, he sees Cas walking over towards them in Misha's suit, but it's ruffled and the tie is loosened around his neck, hair as wild as ever. It looks as if Cas just had a wild heated sex scene, and damn it looks good on him. Although come to think of it, Cas has never had a sex scene before in Mishapocalypse. Dean really wouldn't mind seeing that.

Realizing his thoughts, Dean quickly corrects himself and gives a smile, that hopefully doesn't look as stupid as it feels, and a small nod of his head.

Cas smiles seeing this and when he gets close enough he greets them. "Hello, Dean."

"Hey, Cas."

Cas' eyes drop to the plate of food for a moment, his eyes lighting up a little more in amusement before  
looking to Sam. "And you must be Sam, it's nice to finally meet you. Dean has said nothing but good things about you." Cas stretches out a hand and Sam happily takes it with a firm shake, and out of the corner of his eye he gives  
Dean a smug look.

Dean rolls his eyes. "Don't let that go to your head. You're still a pain in my ass."

Sam smirks turning his attention back to Cas and they drop their hands. "It's a pleasure to meet you too. I'm a huge fan of your work."

Cas smiles warmly at the compliment. "Thank you."

"Though Dean here," Sam starts with a smile to his brother and Dean quickly cuts him off.

"Ooookay, I don't know where that sentence is heading but it's stopping there." Dean claps a firm hand on  
his brother's back with a nervous laugh. Sure Cas may already know what a huge fan he is, but Sam could easily exploit so many other secrets about him that Cas doesn't know. And he would do it just to embarrass him.

"Do I not get a hello? Maybe a thank you for taking time out of my busy schedule to come get your buddies?" Cas turns an icy glare to his brother and Gabriel hold up his hands backing away slowly. Cas is still a bit salty about Gabriel practically forcing him into this situation. "You're right, no thanks needed. They're my friends  
too. You three have fun. I value my life so I'm gonna go." As Gabriel makes his leave, someone shouts to him from across the set and he yells back to them to un-wad their panties.

Cas turns back to them with a regretful smile. "I apologize for not being here to greet you," Cas looks over to Dean with the almost empty plate. "But it appears Gabriel understood how to occupy you until I was free."

Dean grins wide holding up his empty plate in the form of a toast, happily chewing the last bit of food. "On a side note, the food's great."

"I'm glad you like it."

Sam chuckles shaking his head. "When it comes to food Dean will eat anything."

"Not anything." Dean defends as he throws his plate away. "I won't eat liver. That is just nasty."

Sam shrugs. "Dad liked it."

"Dad also fucked over his taste buds when he was a teenager." After this, Dean turns his attention back to Cas, who is still looking way too much like sex for his own good. Like, seriously! He typically has sex hair, but group it together with that rumpled suit and he is practically radiating it. Stopping himself from thinking any further on that subject, Dean shifts gears. "So, Cas, what first?"

Cas casts a glance over his shoulder as if assessing where to go. "They're filming over there, so we can head to set two." He looks back to the brothers. "It's Misha's living room."

"Awesome." Dean grins widely and just as they're about to head over to the set, Sam spots blonde curly hair.

Cas follows his gaze and smiles back to Sam. "She isn't busy right now if you would like to go see her."

Sam looks back with wide eyes as if he'd been caught doing something bad, and he's about to refuse when Dean elbowed him. "You know you want to. Just go, Sammy."

Sam's eyes glide between his brother and Cas. "Are you sure it's okay?"

"Of course."

This might actually be a great time to talk to Dean about what Gabriel had asked of him. Thinking about bringing that topic up, though, starts a storm of the butterflies in Cas' stomach. He absolutely hates lying, and he hates it even more because it's to Dean. If Dean finds out about him lying and going behind his back, will he not want to be his friend any longer? Cas relationship with Dean could be put on the line seeing it isn't as sturdy as Gabriel, Charlie, and Sam's are with him. They only just met, and where the others are used to pulling stunts like this on Dean, Cas might not be able to get away with it.

Sam looks between him and his brother and slowly nods. "Okay," It's quiet at first, but then he repeats it louder, a smile tugging at his lips. "Okay, thank you." And he turns, leaving them alone.

Dean looks over to Cas with a small smile, but when he sees the nervous glint in Cas' eyes, his smile falters. Cas looks like he's gonna have some kind of panic attack. His skin looks faintly paler than usual, but perhaps it's just from the fluorescent lights. Although Dean doubts it. That look plastered on his face is really throwing Dean off kilter and is making Dean worried.

"Cas, you okay?"

Cas' eyes widen for a second as if he forgot Dean was standing beside him, and he quickly schools his expression. "I'm okay."

Dean thins his lips giving Cas a once over. "You sure? You had me worried for a second."

Cas furrows his brows together. "Why were you worried?"

Dean gives him an incredulous look. "Well, it looked as if your skin was getting pale and the look in your eyes made it seem like you just got war flashbacks." Dean pauses for a moment to gauge Cas' reaction, but when Cas only looks confused, Dean continues. "You sure you're good? If it has to do with Sam leaving and possibly getting you into trouble I'll go hunt him down."

"No, no, it isn't-" Cas quickly says then stops abruptly, hand making its way to his own shoulder to rub the tension out. "Sam is okay. I'm sorry for causing you to worry, I was just deep in thought." Cas flashes him a small smile to reassure him that everything really is okay.

That must have been an intense thought, Dean thought to himself, then nods. "Alright." He claps his hands beaming a smile in the actor's direction. "Where to?"

Cas is thankful for Dean letting it go, even if he didn't believe what Cas said to be true. He doesn't know what he would have said if Dean persisted. Perhaps Dean stopped because he himself isn't fond of when people push into his business when he'd rather drop it. That thought is enough to comfort Cas for all of a minute before he remembers he did exactly that. Not intentionally, but he did still get information about Dean when Dean didn't want it shared.

Aaaand Cas feels sick again.

Doing everything in his power to quell his nerves, he leads Dean through the warehouse until they come to a set that is rather far away from where everyone is currently. Dean's eyes shine with delight when they stop in front of it, the lights are turned off so it was dark, but Dean knows this set like the back of his hand. It's Misha's living room.

Cas mutters for Dean to wait a second before he disappears. Dean watches him leave somewhere then all of a sudden the stage lights flick on and Dean's attention is drawn back to the now lit stage. Cas comes back a few seconds after, and Dean doesn't even try to hide the smile from creeping on his face. He glances to Cas wiggling his brows to show his excitement, and Cas smiles warmly. Seeing Dean this happy is enough to relinquish any fear Cas had previously.

Cas waits a couple seconds before walking over to the stage, glancing back over his shoulder to Dean. "Are you coming?" Dean doesn't have to be told twice, he's by Cas' side in an instant. The moment his feet clack on the hardwood floor, his heart soars. He runs a hand over the back of the couch in the middle of the 'room', making his way around to the back to look at all the picture frames and honorary plaques mounted on the wall.

Dean stops at a specific plaque and smiles. He remembers the episode where Misha got it. It isn't an official plaque, this one is actually made of paper, and it's signed by everyone in Misha's department. It had been a grueling mission for Misha, and everyone considered it a lost cause, Matt told Misha to come back, but Misha refused. Misha ended up losing his position in the department because he refused to give up on these people. Of course, Misha reigned victorious in the mission, even without the FBI's help. His department made this paper for him when he returned home. Misha may not have gotten his position back because the higher-ups were pissed at him for not listening, but it didn't matter.

"That episode was one of my favorites," Cas says behind Dean.

Dean glances over to him then back to the paper in the frame. "It was one of my favorites to watch."

Cas turns his head towards Dean, and after a moment Dean does the same, their eyes locking for what feels like a very long time, and actually turns out to be a very long time. Cas sees something spark in Dean's green eyes, something like desire, and Cas internally curses Gabriel. If he hadn't told Cas that Dean might be bi, then Cas's mind wouldn't be making these things up right now. Now, looking into Dean's eyes, it's making Cas want to kiss the man.

Cas can't deny that from the moment he met Dean, he felt his heart skip a beat. Not because he loved him or even that he wanted to get into a relationship with him, but because Dean is the most beautiful man he's ever seen, and Cas still thinks that; even more so now.

The thing about those feelings is that Cas has been desperately trying to subdue them because he doesn't want to make Dean uncomfortable or let his mind get carried away like it is now. His brain is projecting what he wishes to see in Dean's actions and expressions, his little quirks of his brow and the twists of his lips into a smile. The longing Cas sees in Dean's eyes isn't really there. It's all in his head, and Cas is painfully aware of that.

Dean, on the other hand, is thinking the same thing. He wants Cas to want him, but at the same time, he knows it isn't right. He can't be giving Cas sexy eyes because that will make Cas uncomfortable and the fact that Cas probably gets that on a daily occurrence with all his fans makes Dean abruptly stop his eyes from trailing to Cas' lips and stops Dean from licking his lips. It would be nothing new to Cas, to have a fan desire him, but Dean doesn't want to be one of those fans. Cas is here to be his friend. He doesn't need Dean projecting his closeted emotional baggage on him. Cas deserves better than that.

Dammit, Dean, keep it in the closet! He yells at himself before turning away.

Cas sees the sudden shift in Dean as he turns his head back, and it makes Cas squint his eyes and tilt his head in puzzlement, but he says nothing and slowly looks back to the other pictures. The two of them make their way around the room, Cas and Dean both sharing opinions on the decorations and the set itself. They eventually end up sitting on the couch and Dean throws an arm over the back, eyes cast out to the dark of the warehouse.

Cas has tried multiple times to bring up his past relationships, but each time it catches in his throat, and if Dean has noticed him trying to say something, then never saying it, he doesn't say anything, which Cas is again thankful for. He isn't used to this and he doesn't know how to go about it. It doesn't feel natural and he feels as if it isn't something that he can casually bring up out of the blue, so instead, he keeps quiet and waits for the opportunity to present itself.

After some time, something in Cas' pocket beeps at him. He retrieves it and glances at the screen before looking up to meet Dean's curious stare. "Would you like to see the hair and makeup trailer?"

"Would I ever," Dean says without hesitating and the two of them make their way to the trailer.

When the pair gets to the trailer, Cas goes in first so the women aren't confused as to why a random man came in, and Dean follows him. The girls look back and see Cas, then their eyes flick to Dean and the girl with blonde hair smiles playfully meeting Dean's stare, and being the shameless flirt that he is, Dean smiles back.

"Castiel, who's your friend? He guest starring on the show?"

"No, he's not an actor."

The blonde's eyes widen and she looks to Dean again. "Really?"

Dean shrugs in a relaxed manner. "Really."

The blonde hums sizing him up. "Maybe it's for the best. With looks like yours, you'd be eaten up so fast you wouldn't know what hit you."

Cas can't deny that that's true, but his stomach twists at how easy she's flirting with Dean, and Dean seems to be enjoying it. The world really is unfair sometimes. He wants to be able to flirt with Dean openly, not that he's good at flirting but he'd sure as hell give it a try, or even better, Dean openly flirt with him.

After that, the women get to work on Cas' hair and makeup. The blonde occasionally flirting with Dean saying he can come by anytime to get his hair and makeup done, and, of course, Dean flirts right back.

Dean has to admit, the blonde is attractive, and her flirting is appreciated, but for reasons other than most would think. If it weren't for her flirting, Dean wouldn't have anything else to focus on besides Cas leaning back in a black leather chair getting pampered and cleaned up, and Dean would most likely be drooling. They would have to ask him to leave, and that would make him sad.

Cas' eyes are closed, his dark lashes laying on his cheeks. His hair getting slicked back, and his outfit being straightened out. Cas' lips are parted slightly as the other woman does his makeup, and Dean can't fight the urge to lick his lips and pull his bottom lip between his teeth because damn he looks so good right now.

When the women are done, Cas stands up and looks in the mirror for a second before turning to Dean. Dean closes his legs and looks him up and down, mouth open slightly in what could be interpreted as desire, but Cas brushes it off as his mind projecting again.

"Shall we go?" Cas offers a smile and Dean only nods, not trusting his voice to not sound wrecked. They leave the trailer, the blonde winking at Dean as they leave.

Trying to think of something to get his mind off Cas looking devastatingly handsome before Dean gets himself into an awkward situation, he says the first thing that comes to his mind. "Those girls seemed nice."

Cas glances to Dean for a second before turning his attention back forward. "Tammy seemed to think you seemed nice too."

Dean bites his bottom lip. "You caught that?"

Cas scoffs with a faint roll of his eyes. "Pamela would have caught it and she's blind."

"It was that bad?"

Cas arches a brow at how nervous Dean sounded just now. When he looks at his face, Dean looks slightly uncomfortable. "There isn't anything wrong with it," Cas says looking back. "she's a nice woman. She flirts with almost everyone, but she's nice."

Dean takes that and runs with it, a smile tugging at his lips. "She flirt with you too?"

Cas nods. "Yes, back when the show started, but I-" Dean arches a brow at the abrupt stop in his sentence. "I was seeing someone back then so it felt wrong. I asked her to politely stop and she apologized immediately." Cas sees Dean open is mouth then quickly close it looking away. It's obvious Dean is curious, but would feel uncomfortable asking, so Cas makes it easier on him. "The relationship itself didn't last long, if you could even call it a relationship, he … it wasn't a life he wanted and I respected that, so he left."

Dean's head turns to Cas, a shocked expression on his face, questioning whether he heard him correctly or not. "You're…"

"Not gay, if that's what you're going to ask." He turns his eyes to Dean with a soft smile, and a light blush creeps across Dean's face.

"Sorry," Dean mutters embarrassed.

"It's quite alright, Dean."

There is a long pause, Cas not saying anything else as he lefts Dean process whatever it is he's thinking. When Dean speaks up again, it's quieter than usual. "So, you … are you bi, or-?"

"I don't like to identify with any particular sexuality, but to put it in terms for you to understand, you could say I'm pansexual." Cas glances to Dean once more to see him deep in thought.

"How long have you…?" Dean doesn't have to finish his sentence for Cas to understand and Dean is thankful for that.

"Since I was young. I was in middle school."

"Wow," Dean says quietly and drops his eyes to the ground with a smile and he turns it to Cas for a second. "That's pretty young to find out. Wish I-" he bites his lips and looks away with a chuckle. "I never even knew there were different sexualities until I was in high school." Dean rubs the back of his neck sheepishly. "Don't know how I avoided that topic for so long, coulda been my dad now that I think about it, but-" Cas narrows his eyes trying to piece what Dean is saying together with his actions. He doesn't want to say anything to interrupt Dean from opening up because if it comes to it, Dean may mention something about questioning his sexuality. Dean shrugs off what he was going to say and shoves his hands in his pockets, his palms becoming sweaty from his nerves. "So how'd-" He stops talking and clearly looks uncomfortable with the question he wants to ask, and Cas gets the gist, but Dean speaks up before he can answer. "How'd you know?"

Cas is silent for a little while, not looking in Dean's direction, playing ignorant to the fact that the question is basically Dean asking how to figure out his own sexuality. "I don't think there was a specific time that I realized it, but more a series of events. At that time, I was watching everyone get into some kind of relationship. A few girls even asked me out, but I didn't want to be in a relationship with them. I thought there was something wrong with me for not desiring to be in one, seeing as everyone else my age, that's all they were doing." Cas pauses for a moment and squints his eyes in a way Dean hasn't seen before. It's as if he's in pain. "I, unfortunately, found out the hard way. I formed feelings for my best friend. He wasn't too thrilled about when I told him. He told me he didn't want to be friends with someone that's defective." Dean thins his lips. He can only imagine how painful it would be to be rejected so harshly, especially at that age. "I don't let it bother me anymore. It was in middle school, everyone is unpleasant in middle school. I actually thank him now," Dean turns to give Cas a very perplexed stare and Cas elaborates. "Without him, it would have taken me a lot longer to understand myself and I might not be as comfortable with who I am today because of that."

Dean frowns and turns his eyes away. "Still, that's gotta hurt."

"Oh, it did, but thankfully I wasn't too deep in infatuation with him so I got over it quick enough."

"That kid, did he spread rumors about you?"

Cas doesn't want to pick up on the pain in Dean's question, but it's inevitable. The pain as clear as day. Had Dean come out to someone he thought he could trust and they threatened to spread rumors about him? Is that why Dean doesn't want to come out? The thought made Cas' stomach twist.

"No," Cas says with a confused frown and he regrets the tone in his voice the moment it leaves his lips because Dean has visible walls that shoot up when he hears the question in Cas' tone. Cas curses himself. It had been going well. Of course, he had to fuck it up and make Dean close off. He thins his lips not wanting Dean to close off to him, but part of him feels that he could help; he wants to help. "Dean," Cas starts a little tentatively and Dean refuses to meet his gaze, but Sam chooses that exact moment to shout at them.

"Dean, Cas!" Sam waves his arm in the air, Gabriel is beside him. Cas can see Dean visibly relax knowing Cas isn't going to get to finish his question.

"Sam, done with Jess already? I thought I would have to drag you away from her."

"I did that for you." Gabriel smiles. "Jessica and Castiel here have work to do, therefore I am back on Winchester duty." Gabriel smirks and looks over to Cas who is looking at Dean with an emotionless stare, but Gabriel knows his brother well enough to know that look is so much more than what he's showing. Gabriel looks back to Dean making sure his smirk doesn't leave his face. Dean doesn't look tense or upset, but apparently, Dean is a good actor when it comes to emotions, so Gabriel knows something went down. He'll just get it from Cas later. "Go on Castiel, I am relieving you. Be free."

Cas tears his eyes from Dean to look at his brother. Then all of a sudden his phone rings. Cas' brows scrunch and he takes it out of his pocket, Michael's name is sprawled across the screen. Cas audibly groans and answers it stepping a few steps away from the group. Dean arches a brow at the groan, he thought they all got along.

"Yes, Michael?" There's a muffled voice on the other end and Cas' face scrunches in distaste. "No … Can't we do that later? … I told you it isn't of importance … Michael-" Cas rubs his face looking exhausted. "Fine." And with that Cas hangs up abruptly and comes back to the three.

Gabriel arches a brow shoving his hands in his pockets. "Everything good?"

Cas sighs looking rather irritated, which is a first for Dean. He's never seen him ever look anything other than passive, happy, worried, or any other emotion similar to those, but never outright irritated. The look is actually rather intimidating.

"No." Cas calms his expression and looks to Sam and Dean. "I'm sorry. Something has come up, It appears my schedule has been booked without my knowledge and I won't be able to see you again today." A frown etches its way onto his face. "I really am sorry."

"Hey, no worries." Dean waves it off. "Things come up, it's no big deal."

"It is. I told you to come today because I was told my schedule for shooting ended after this last scene."

Dean can see how upset Cas is by this unexpected schedule change, and he hates seeing Cas like that. "Cas, it's okay, really. Sam and I, we both had a great time today. You're a busy man, we don't expect you to form your schedule around us just because we're here. If you gotta get things done then, by all means, man, go. We can meet up again another time."

"Dean's right, Cas," Sam adds with a smile. "Today was fun, thank you for inviting us."

The frown on Cas' face doesn't leave but he nods.

"I can help 'his majesty' with whatever it is he needs." Gabriel offers.

"I wish you could, Gabriel." Cas sighs. "He wants something to do with the show."

Gabriel arches his brow. "Cas,"

Cas knows what Gabriel wants to say, but won't, at least not in front of Sam and Dean. He'd tell him to tell Michael to shove it and to not give into him every single time. Which isn't true. Cas most certainly does not give in to Michael's every demand. He just happens to give in to ninety percent of them. So instead of answering Gabriel, he turns back to the brothers.

"It was nice seeing you again, Dean. And Sam, it was a pleasure to meet you. I hope to see you both again soon."

They say their goodbyes and after watching Cas disappear, the brothers talk to Gabriel for a few more minutes before leaving Gabriel alone to head home.

Gabriel sighs running a hand through his hair muttering to himself. "Well, this isn't how I thought today would go."

XXXXX

The whole ride home, Sam noticed something … off about Dean, but he keeps his mouth shut until they get home. Dean is in the living room, flopped out on the couch when Sam speaks up, sitting in the chair beside him.

"So, did you enjoy the private tour with Cas?"

Dean scoffs. "Are you kidding? I fucking loved it, Sammy."

Sam nods, a smile playing at the corner of his mouth. Dean is clearly still feeling like a kid in a candy shop; giddy and left wanting more. "So where did he take you?"

"Misha's living room. I got to see the paper plaque." Dean looks over to his brother with a wide grin. "Jealous?"

Of course he is. "No." He lies, but Dean only beams more, catching the lie easily. Sam thins his lips, worried about Dean closing off when he asks what he's going to ask. "So," Dean arches a brow at his tone. "Did you and Cas talk about something?"

Dean furrows his brows. "Why does it matter what we talked about?"

Sam shrugs lightly. "Because there's a weird air around you since I came back from talking to Jess, I'm just worried something happened."

"What would possibly happen?" When Sam doesn't answer, Dean nods. "Exactly. Sam, you're worrying about nothing."

"Yeah, I guess." Sam shakes his head running a hand through his hair. "Sorry."

"It's all good, Sammy." Dean forces a loud yawn and stretches over the back of the couch. "I'm heading to bed. I'm beat. See you when I see you."

Sam nods watching Dean disappear up the stairs, his eyes falling on the clock in the kitchen when he disappears. Even though Sam knows something's up, he isn't going to push it, not right now. Sam may want to help Dean with everything, but when Dean goes to 'bed' at seven in the evening, Sam knows to leave him alone. He just hopes it'll all work itself out.


	7. Chapter 7: Coming To Terms

I have no excuse to why I haven't updated in a month, so I'm sorry if anyone was wondering if I abandoned this work. I've finally finished this chapter though! Even if it is a little short and I kinda cringe posting it, but I don't know how else to make it better, but that all aside I hope you enjoy!

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Chapter 7: Coming To Terms

Something is off, that much Sam knows for sure. Ever since they visited the Mishapocalypse studio those few days ago Dean has been wandering around lost in thought, whatever it is constantly wearing on his mind. Whatever those two discussed, it impacted him.

Sam isn't an idiot though, he is pretty sure he knows what it's about, but he isn't going to butt into Dean's thoughts right now, he knows when to put on the breaks when it comes to Dean. When Dean is typically in this state of mind, Sam gives him a week before he confronts him to ask if he's all good. Right now he wants to give Dean time to process whatever it is he's thinking about because the more Dean accepts it himself, the more accepting he'll be when Sam will confront him about it. Because yes, Sam is inevitably going to confront his brother about it, but he wants to wait until he knows it's the right time so it won't cause Dean to take five giant steps backward.

So here Sam sits at the kitchen table, laptop open, waiting for the water to start boiling on the stove, and working on his essay while listening to the pitter-pattering of Dean's socked feet pacing around his room upstairs.

' _It'll all be fine._ ' He tells himself as he sips at the water in his glass. ' _It always is._ '

Meanwhile, in his room, Dean is pacing the length in his room, turning around, then pacing the width, then finally pacing in a big circle. He wished, _prayed_ , that these feelings weren't real and they were only in his 16 year old brain. He can deny it all he wants, but no matter how hard he tries, they keep coming back. It isn't the fact that he likes men, although he still can't say it out loud, what is really bothering him, what he can't, for the life of him, is get _him_ out of his head. He has tried imagining women laying naked in his bed. Their curves, long lashes, smooth skin, beautiful blue eyes, dark brown hair, strong abs, that smile that wrinkles the skin by those captivating cerulean eyes.

Dean screams in frustration and tears his door open, storming down the stairs to the front door. Sam looks at him, worried as hell.

"Dean, what's wrong?" Sam says starting to stand up.

"I'm going for a run!" Dean's voice is irritated, and all Sam can do is whisper 'run?' as Dean leaves, slamming the door behind him.

Dean sprints down the road at full speed until his lungs feel like they are going to collapse and his legs feel like they're on fire, and then he keeps running.

Every damn time he thinks about anyone in a sexual way, Cas sneaks up in his thoughts, and Dean can't stop it. He's more or less accepted the bisexual thing, but the fact that he's falling for Cas so fast, and so hard, scares him to death. He's only fallen like this once in his life and it ended horribly. Not to mention that Cas is a famous actor and there is no way Dean can be with him. It would only end in blood and tears. They live in different worlds. Dean can't afford to fall in love with Cas, but his heart has other ideas, and it is so frustrating he just wants to scream until he's blue in the face.

When Dean finally stumbles back home, his legs feel like jello and he is heaving fiercely for breath. Sam is still at the table, but the smell of garlic fills the air now. Dean wheezes and leans heavily against the door. "Don't ever … let me do that … again … ever."

Sam simply watches as Dean grumbles to himself, weakly kicking off his shoes, his chest heaving. He wants to ask what made him want to go for a run; Dean hates running. Although if he asks, then it would bring it back up and Dean would get frustrated all over again and who knows what he'd do then. Well, taking his condition into account right now, Sam would say he'd flop on the floor and just pass out with idle threats to kill his brother and never actually going through with it.

Unable to hold himself back, Sam speaks. "Want to talk about it?"

"Not particularly." Dean wheezes, he's slowly catching his breath again.

Sam nods looking back to his laptop. "So you just wanted to go for a run? Really? A run?" Sam huffs a small laugh at that.

Dean snaps narrowed eyes to his brother. "I was just sick of grading tests and wanted to get it out of my system. What's so wrong with that?"

Sam's eyes trail to the floor beside Dean's feet and sees his school bag with all his papers in it. Pulling his bottom lip between his teeth and chews on the soft skin, he gives his brother a suspicious look then nods with his typical, "Heh, uh-huh."

Dean gives Sam an affronted stare, straightening his shoulders. "You try grading tests all day and see how you like it."

"I never said anything about that. I just said okay."

"No. No, you did your little," Dean does his best Sam impression, which is actually scaringly spot on. "Heh, uh-huh." Dean gives him an unamused stare as if waiting for a response, but Sam only shrugs. "That is not just 'okay' in Sam language."

"Look, Dean, I don't know what you want me to say." Sam sets down his water and looking him in the eyes. "If you don't want to tell me then you don't have to, but you know I'm here to help you with whatever it is you're going through."

Dean furrows his brows, is he being that obvious? "I'm not going through anything." He says a little too defensively.

Sam presses his lips into a thin line looking away humming a quiet, "Mhmm."

Dean narrows his eyes. Sam is clearly trying to say something, or he has something he wants to say, but isn't. He knows the look. "What are you trying to say, Sam?"

Sam shrugs as if it's not a big deal. "I'm just saying it's hard to grade papers without, you know, the papers."

Sam looks up from his laptop and meets Dean's stare before letting his eyes dart to the bag on the floor and back to Dean. Dean scrunches his face up and looks over to the living room where he sees his bag. Walking over to it, he grabs it, looking Sam in the eyes as he plods up to his room. Sam sighs running a hand through his hair and leans back in his chair.

Dean throws his bag on his bed and runs distressed hands through his hair. Has he really been that obvious? Yeah, he may have accepted the fact that he's bi, but he isn't ready to have Sam know. But if Sam does know … does Sam think he has a crush on Cas? Has he known this whole time? Dean feels a chill run down his spine. No. He can't let Sam think that. This … this isn't a crush. No. It's just admiration for a well known, amazing actor. It'll go away. It has to. It's just running high because he's becoming friends with Cas, right? And he can't have feelings for him because that'll ruin the friendship. It'll die down. This is all just a phase.

He groans and falls onto his bed. Adults aren't supposed to go through these phases, that's a teenager thing.

It was a few days ago that Dean stopped making himself deny he's bisexual and actually let himself think 'I'm bisexual.' while he looked into the bathroom mirror after a shower. It made his cheeks heat up slightly, and it wasn't from the heat in the bathroom. When he caught himself blushing he told himself it was ridiculous to get embarrassed at just thinking it, nobody but him knew what he was thinking. After he calmed down, he thought it again, and again, and slowly it became a little easier to think it and not flush.

The only problem with finally letting himself think this is that his thoughts went full throttle and started throwing Cas in wherever and whenever his mind could.

Dean is making dinner, his mind supplies that he's making dinner for him and Cas. Dean is in the shower, Cas joins him. Dean is getting ready for bed, Cas is too. Dean wakes up in the morning, Cas is snuggled with him. Dean is grading papers, Cas is there to entertain him through it. Cas is everywhere.

With the whole bisexual thing, he was hoping it would work out so he could see an attractive man and let himself appreciate his looks, but never actually get into a relationship with them. The whole relationship with a man lowkey makes his stomach twist with nerves. He hasn't wanted a relationship with a man before, but now with Castiel, he wants him, he wants it so bad, but every time he thinks about it …

Dean hates himself for being nervous. He hates himself for being such a chickenshit. He hates himself for wanting to ruin their friendship at a chance to be with him. He simply hates himself for letting something that he thought was long buried come up and bite him in the ass like this. The butterflies swimming in his stomach every time he thinks of Cas, then his nerves set in and twist his stomach. He hates himself.

Dean has had a rough time accepting his sexuality. Once, back in high school, he tried to come out to someone he called a friend, but that ended horribly. His 'friend' basically told him that if Dean's coming out wasn't some kind of joke, then he was going to spread rumors about him, blackmail him, and everyone is going to tease Sam for having a fairy faggot for a brother. Obviously, Dean laughed it off, even though he felt sick to his stomach, saying it was a joke and that his 'friend' should have seen the look on his face.

That friend was Dean trying to test the waters, see what it felt like to come out. Turns out that test run had felt awful and made everything that much more difficult. If it had gone well, he was thinking about telling Sam, but after that, the thought of telling Sam and having Sam reject him like that, it made Dean want to throw up, so instead, he locked it up and threw away the key. It was better safe than sorry. But somehow the key has made its way back to Dean in the shape of Cas. Dean feels that maybe … if it's Cas, then maybe …

Down in the kitchen, Sam sighs pulling out his phone and looks at the group chat. He sets his phone down again and taps his fingers on the table. Sam is starting to feel a little guilty for trying to butt into Dean's privacy like this, which is weird because Sam and Dean almost never feel bad about butting into each other's private lives. One time Dean went so far that Sam hadn't talked to him for two weeks. Although there is something about this that Sam feels that it's a little different. It's something new. Dean has never had something like this happen before, and maybe by inserting himself and everyone else into it, it is going to make him crash and burn. Maybe … maybe they shouldn't be doing this. Dean seems to be genuinely trying to work this out himself, and it may take him some time, but he'll be able to do it. Sam knows Dean can.

With that is mind, he picks up his phone again and types out a message.

 **Sam: Guys, I don't think we should be doing this.**

After a minute, Gabriel is the first to respond.

 **Gabriel: Getting cold feet, Winchester?**

 **Sam:** **It's not that. It's just the more I watch Dean, the more I realize he may not need our help.**

 **Charlie: I've been thinking about it too. I want to help Dean as much as I can, but what if he finds out? He's gonna be mad.**

 **Sam: Mad is an understatement.**

 **Sam: I'm just not sure he needs our help. Dean just went for a run a little while ago.**

 **Gabriel: This is worse than I thought. Dean needs our help more than ever. Running? That's bad for you.**

 **Charlie: Dean Winchester is running?**

 **Sam: A run, singular, but it's a start.**

 **Charlie: Well, whatever you decide to do, Sam, I'll stick with you.**

 **Gabriel: Are we being disbanded?**

 **Sam: I'm not sure… maybe it's for the best.**

 **Gabriel: This was the shortest lived intervention I have ever been a part of, and I barely got to do anything );**

 **Castiel: I think it is a good idea that we stop.**

 **Gabriel: Cassie! You're here!**

 **Gabriel: Hey, I've been meaning to ask, what went down when you and Dean got you alone time? ;)**

 **Castiel: Stop being immature, Gabriel, I am not going to discuss what Dean and I talked about.**

 **Gabriel: But Caaaaas …**

 **Castiel: No, Gabriel. Sam, Charlie, please don't let my brother convince you that continuing this is best. I have a hunch that this is much more than just a sore subject for Dean. Pushing him might end horribly.**

 **Gabriel: So something did happen?**

 **Castiel: Gabriel.**

 **Gabriel: I'm not trying to be 'immature', I was genuinely worried because of that look you gave him. Just … is he good?**

 **Castiel: I don't know.**

 **Sam: I'll make sure he is, thanks for understanding you guys.**

 **Charlie: No problem! We'll always be here for you.**

XXXXX

Dean sighs as he sits on the couch in the teacher's lounge for lunch, he wants to just go to sleep; he hasn't gotten much sleep in the past couple days. He closes his eyes and lays his head back on the couch, but the door soon opens and a bubbly "What's up, bitches?" follows the noise of the door closing.

Charlie's eyes land on Dean and she swears she could see a rain cloud hovering over his head. Grumpy-gloomy-Dean is no-fun-Dean. She thins her lips thinking back to the conversation she had with everyone last night. She's not doing this for Team E.L., she's doing this as a concerned friend that hates to see others upset. The world should be happy.

She slowly walks over and sits on the couch. "You feeling okay, Dean? You've had this cloud of negativity shrouded over you for a few days now."

Dean runs a hand over his face and sits up, not looking in Charlie's direction. "Fine, just been tired." Charlie's eyes don't waver from him, giving him an unconvinced stare. Dean can feel the stare boring holes in him and he looks over at her. "Really, Red. I'm fine."

"If you're fine then lose the ever looming negativity cloud, and if you can't do that then talk to me because you're starting to scare the students."

Dean rolls his eyes and opens his mouth to say something, closes his mouth, sighs, runs a hand through his hair, and finally manages a weak, "It's-" before groaning and grumbling to himself. "Nothing, it's nothing. Just something Sam said to me."

Charlie remains quiet for a minute, gauging what Sam could have said to him. "I may not know what you two were talking about, but whatever Sam said, I'm sure he's just worried about you."

"That's what he keeps saying. What does he have to be worried about? I-" He cuts himself off and rubs his face again. This whole situation clearly making him slightly uncomfortable. "He has more important things to be doing than worrying about me."

Charlie gives him a small smile and puts a gentle hand on his knee making Dean move his hands from his face to look at her. "Your brother cares too deeply about you to ever stop worrying, just like you worry about him. If you have something going on in your life, no matter how big or insignificant it may be, Sam will always be there for you. Like it or not." She gives him a warm smile. "Talk to him, even if there isn't anything going on, it might loosen the tension and make our section of the school feel less like a war zone of man pain."

Dean gives a weak smile and thins his lips. As much as he hates to admit it, she's right. Dean will man up and talk to Sam about it once and for all.

XXXXX

That night Dean convinced himself that he is going to say it. He is going to tell Sam that he's bi.

Right now Dean is making dinner waiting for Sam to come home, counting the nonexisting ticks of the clock as the seconds roll by. Dean is so lost in thought that when the front door finally cracks open, Dean jumps a little, his heart jumping with him. Dean looks back and steels himself.

"Sam?"

"Yeah?"

"Can I talk to you for a sec?"

"Yeah," Dean can hear the surprise and curiosity in his brother's voice. Sam rounds the corner in the kitchen's dining room. "What's up?"

"I've been thinking," Dean sighs already not sure how he should continue. Should he just blurt it out? Should he even say it at all? "I don't want you worrying about me, but I know even if I tell you to not bother, you'll still do it." Dean shrugs. "That's who we are. And I know I've seemed … occupied recently, I've just had something running through my head is all. You don't need to worry about it though, I'm good."

Dean meets his brother's eyes indicating that he's done talking because yes, he chickened out again.

Sam nods slowly. "Okay."

Dean nods and pats the counter. "Thanks, Sammy." He then turns around and proceeds to make dinner. He tries making small talk about what they're having for dinner to shift gears, but there's a weight in Dean's stomach that won't go away.

Sam's mind is running in circles at Dean's sudden desire to talk about what's going on, even though he didn't really say what's happening, but it's a step forward. Sam can't help but wonder if Charlie had said something though. She had to of said something, right? Charlie has been his best friend for years now, so maybe she did. Does that mean Dean's accepted his feelings, or is he on the verge of accepting them?

Dean thins his lips, his heart rate picking up speed as he comes closer and closer to blurting out what he wanted to say from the get-go. It bubbles up in his stomach and works its way up his throat. He's opened his mouth a few times now, but it hasn't made it past his lips. He stops thinking about it and his heart slows back to a normal speed, then he goes to say it again and it speeds up again and he stops.

Dean is growing angry. Why is this so hard? Just say it already. _'Sam, I'm bi.'_ that's all he has to say. Three little words. Easy. Now say them.

Dean is facing the stove still cooking their dinner. He can't look at Sam when he is going to say this. Call him weak and spineless, but this is the only way he is going to be able to bring himself to say it. He bites his bottom lip and takes a little breath opening his mouth and quietly says, "Sam," He cringes at how quiet it came out, but there isn't any going back.

"Yeah?" Sam says from behind him.

"I …" Dean groans at himself and slams the spoon on the counter with an irritated, "Dammit!" he turns angrily to Sam. "I'm bi!"

Sam's eyes widen only a hair as he looks into his brother's eyes. He wasn't expecting Dean to actually say it, let alone shout it. Sam soon sees Dean lose his confidence and shrink back into the counter, eyes darting away, clearly nervous because Sam is just staring at him, and Sam can only guess what his face looks like, so he quickly corrects his face and says, "Okay."

Dean looks back to him a bit surprised. Sam genuinely looks as if it doesn't surprise him, and part of Dean feels a little offended. It took so much effort for Dean to say that, and his heart was working overtime to say those two words, and Sam isn't even surprised. That makes Dean start to get nervous again. "Was it that obvious?"

Sam meets Dean's gaze. "Dean, I've had reason to suspect you were bi since you were in high school."

This information is completely new to Dean and he doesn't know how to feel about it. "And you never said anything?"

"It wasn't my place. You had to come to terms on your own time." Sam shrugs. "Never thought it would take you this long through."

Dean frowns as an unwelcome memory crashes into him making him shiver slightly and instinctively put up mile high walls. Sam sees this and it's a shock for a few reasons. One, Dean's already come out as bi. Sam thought that was the reason behind everything in the first place. And second, Dean has never put up visible walls around himself when it was just him and Sam before. Never. Sure Dean may lie about things, but never has he closed himself off so far that Sa can _see_ the walls. Sam's guts twists with worry. Something bigger is going on here, and he has no idea what it is.


	8. Chapter 8: What's Life Without Taking

**Chapter 8: What's Life Without Taking Chances**

It's been two weeks since Dean and Cas have seen each other, or really even texted, since Cas is always so busy with work. So when Cas texts Dean and asks if he and Sam would like to come to set again, Dean is thrilled. Although Dean wonders how having them come so often is okay, but so far it's the only way they can hang out seeing this is Cas' busiest time for filming.

Dean isn't complaining though, he loves being able to go on set for Mishapocalypse, contrary to popular belief, it doesn't take the magic out of the show. Although, Dean has to admit he would like to be able to hang out with him outside of his work sometime too. Granted Dean and Cas have only known each other for a few weeks, so Dean is just being impatient.

Dean and Sam roll up to the parking lot for warehouse 13 and head up to the door where Berry the bodyguard is standing stoically.

Berry turns his eyes to the brothers when he sees them walking towards him. "You two again?"

Dean smirks at him. "Don't act like you aren't happy to see us, Berry."

Berry simply rolls his eyes at the older Winchester and informs whoever is listening over the walkie-talkie that the Winchesters are here. It isn't before long that the door opens and Cas smiles at them both.

"Hello, Dean, Sam."

Cas steps aside for them to come in and Dean smirks at Berry and throws a, "Stay awesome, Berry." at the bodyguard, then smirks at Cas walking past him saying, "Greeted by the man himself, what do we owe this honor?"

Cas, not really understanding it's a joke, answers seriously. "Gabriel isn't here today and I wasn't filming."

Dean can't stop himself from laughing at how serious Cas answered. Cas then proceeds to tell Sam that Jess isn't filming currently either if he would like to talk to her, but he doesn't have to. Of course, Sam ditches them though after thanking Cas for the invite. Dean laughs at how eager his little brother is to see Jess, then he turns to Cas with a smile as they start to walk away from the entrance.

"So, what do you have planned today? Walk on the beach? Climbing Mt. Everest? Visiting Machu Picchu?"

Cas' smile warms Dean to the core, seeing the crinkle by his eyes. "I'm sure those would all be very fun, but sadly that will have to wait for a later date. I have to admit though I would love to visit Machu Picchu with you, though I'm sure anything would be fun with you there."

Dean feels his cheeks start to burn at that statement. The only thing coursing through Dean's mind right now is a frantic _'Was that a flirtation?! Oh my God, did Castiel Novak just blatantly flirt with me?!'_ Then Cas adds something that makes Dean's mind grind to a halt,

"Of course it would be fun with you and Sam both there."

Of course he'd add that, Dean thinks. Dean can't stop the pang of disappointment from gripping at his heart. It's obvious he hadn't meant that as flirting. Dean smiles at him with a forced laugh. "I don't know about that, Sammy and I can get at each other's throats on vacations."

"That's what I would be there for."

Dean meets Cas' eyes, his blue gaze feeling like it cuts right through Dean's very core. Dean thins his lips and chews the sensitive skin on the inside of his lip. He wants to tear his eyes from Cas', but it's like he's in some kind of trance. That is until a woman walks up to them and her voice snaps Dean's attention to her.

"I'm sorry to interrupt, but," She meets Dean's eyes who is still acutely aware of Cas' gaze on him. "Are you an actor here?"

Dean collects himself and clears his throat, making sure it won't crack or do anything to embarrass him. "No, I'm just," Dean nods in Cas' direction. "Cas' friend."

Her eyes widen and she looks between the two men before her eyes lock on Dean again. "I'm surprised you aren't an actor. You seem like you would be great at it." She waves her hands starting to get nervous. "Sorry, I just … I saw you here once before and I couldn't stop thinking about it so I had to ask."

Dean gives her a flirty smile, trying to distract himself from Cas' eyes staring him down. "Yeah, I've been here once before. Wish I could have seen you the first time though." She blushes, but before she could respond someone shouts for her and she apologizes and leaves. Dean feels suddenly nervous now that he's alone with Cas again. He feels like he's done something wrong, but he doesn't know why he feels like that. It isn't like he actually did anything bad. Dean gathers his courage and looks back into Cas' eyes. They don't speak for what feels like hours, but Dean knows it's only been a few seconds, then Cas thankfully breaks the silence that's strangling Dean.

"She's right, you know."

Dean arches a brow at that. "About what?"

"I'm sure you'd be a great actor."

Dean huffs a laugh and looks away shaking his head. "I may be able to lie with the best of them, but acting? No way. That's your specialty."

Cas goes to speak, but when he opens his mouth someone shouts at him that they need to ask him something. Cas sighs running a hand through his already messy hair. "I'm sorry, I'll be right back."

"No problem, man."

A few seconds after Cas leaves Dean standing alone, Sam comes back over. His arms are crossed over his chest looking between Dean and Cas, huffing a small laugh. He was all the way across the room and Sam could still see the eye sex going on between them, and seeing how Dean came out to him already, he can't stop himself from saying, "Just fuck him already."

Dean sputters and chokes on air, sending himself into a coughing fit. When he's done coughing he gives his brother a shocked look.

Sam raises his brows and uncrosses his arms. "Too soon?"

Dean collects himself and casts a couple glances around to see if anyone was close enough to hear what Sam had just said. Yeah, he may have come out to Sam, but he isn't exactly ready for the world to know. "No, you just … surprised me." he manages to mutter.

Sam watches Dean scan their surroundings looking a little nervous. "You know nobody will care, right?"

Dean sighs rubbing the back of his neck. Yes, he knows that, but part of him can't stop being nervous about it. "Some people will."

"Who cares what they think? Why should their opinion matter to you anyway? Don't let a couple people's views stop you from being happy, Dean." Sam pauses for a second and debates whether he should bring this up or not, but then decides that it hasn't stopped him this far. "Why don't you ask him out?"

Dean shoots wide eyes at Sam. He doesn't have to say who he's talking about because it's obvious. "No fucking way." Dean hisses in a harsh whisper and Sam gives him his famous bitch face. Dean sighs and speaks quietly. "Sam, I've only just come to terms with the whole 'feelings for a guy' thing, I'm not ready for a relationship. I could end up hurting Cas." Dean runs a hand down over his mouth feeling a little nervous again. "Plus it … I still get a weird feeling every time I think about it."

"Why?" Sam frowns, concerned, but Dean remains quiet. "Is it because of what dad taught us when we were younger? Dean, who cares what he thinks."

"I do, okay?" Dean snaps in a whisper. "I can't help it. Every time I think about it I imagine the look of disgust on his face, how disappointed he would be in me. Having a, in his words, 'fairy faggot for a son' isn't something he'd accept." He stops and tears his eyes from Sam. "I can't, Sammy. Not yet."

If Dean were being honest with himself, the main reason behind not wanting to ask Cas out is that it more scares him than makes him nervous. Not because he fears rejection though, but there's no way Dean is gonna tell Sam that.

Dean has had some baggage from his past that he thought he had let go, but apparently it's rising back to the surface to fuck him over again because of course it would. Of course it couldn't leave him alone and let him carry on with his life without making his stomach twist at a mere thought. He has to take care of his baggage before he can even think about dragging Cas into it, and there would be no way of explaining it to Sam without spilling what he's kept locked up for years now. He never wants Sam to know, and he will keep him from knowing for as long as he can so Sam can keep seeing Dean like a little brother is supposed to see his big brother.

So yes, Dean is just going to let Sam think it's all because of their father. But damn if it doesn't make Dean feel like such a pathetic coward for letting it affect him like this after so many years. He's supposed to be a tough warm red-blooded American heterosexual man, and that means not letting his emotions get the better of him. At least, that's what their father tried to raise him like. But here Dean is, letting his past fucking him over, and he has a giant fucking crush on Castiel Novak.

Sam looks over at his brother and sees the hurt deep in Dean's eyes, the visible walls starting to rise again, so he lets it go with a quiet, "Okay."

Dean quickly switches the topic after that and Cas comes back a few minutes later telling the brothers that something happened with a set and they can't shoot anymore today, so they are able to go to lunch if they would like. The mention of food has Dean's mouth watering. Cas tells Sam he can invite Jess too, so Sam runs over and does just that.

Dean turns his attention to Cas. "So, what set had a mishap?"

"Misha's living room. One of the new tech kids messed up and added the fake explosions to the living room instead of the correct set. Everything is rather messed up."

"You could just use the set and say Misha had some seriously wild sex." Dean immediately wants to take back what he said, but as soon as Cas starts to laugh at it, Dean feels a flutter blooming in his stomach.

Cas smiles up at him, chuckles subsiding, the smile on his face is contagious. "I genuinely doubt anyone could have such wild sex to make a room look like it was exploded."

Dean arches a brow, a smirk on his face, his eyes locked on Cas' blue ones. "Are you saying it's impossible? Because if you ask me, that's sounding an awful lot like a challenge, Novak."

Cas' smile doesn't leave his face, in fact, it almost turns playful. "I am, indeed, saying it's impossible, Winchester."

Before Dean can say what he was about to say, which would have inevitably ended up embarrassing the hell out of him, Sam comes over clearing his throat. Cas and Dean don't break eye contact for a few seconds longer, then Dean breaks away first to look at his brother. Standing beside him is Jess, smiling at him.

"Hey," Dean smiles at her holding out a hand and she takes it. "Nice to finally meet you, Jess."

"You too, Sam has told me a lot about you."

Dean smirks, his eyes turning to Sam. "Aw, Sammy, you talk about me? You sap."

Sam rolls his eyes. "Shut up, I told her how you made me break my arm jumping off the shed when we were younger and had to take me to the ER on the handles of your bike."

Dean drops Jess' hand and points at Sam accusingly. "That was not my fault."

"I only did it because you did it first, Dean."

"That's because I was dressed up as Superman, everyone knows Batman can't fly, Sammy."

"I was five, Dean!" Sam can't help but smile as he exasperatedly tries to make his point.

Dean looks like he's about to argue back, then stops and makes the sturgeon face and nods. "Noted," Dean smiles before adding, "but you started questioning my actions after that. I had to teach you not to follow people just because they do something. Hence, lesson learned." Dean claps a hand on Sam's shoulder grinning from ear to ear. "You turned out pretty good if I do say so myself."

Sam rolls his eyes and playfully shoves Dean away making Dean laugh. "You most certainly did not mean for that to be a lesson. You were freaking out."

"In my defense, I was nine; I'd never seen an arm bend that way in person."

When they finally leave the building after Sam and Dean's little 'fight', which was rather entertaining for Cas and Jess, Sam and Dean get in the Impala and Cas and Jess get in Cas' car and lead the way. They end up in a diner's parking lot, and when Dean gets out of the car he walks to Cas' and looks it over. When he finishes, he looks at Cas, who's watching him curiously.

"This is your car?"

Cas scrunches his brows and tilts his head making him look rather adorable. "Is something wrong with it?"

Dean smiles and shakes his head. "No, it just looks like a pimpmobile."

Cas squint his eyes. "You sound like Gabriel."

Dean laughs and he claps a hand on Cas' shoulder without thinking, but he plays it off as if the notion didn't shake him to his core. "As long as you like it, buddy. That's all that matters."

They make their way inside and claim a booth so it's Sam and Dean on one side and Cas and Jess on the other, with Sam in front of Jess and Dean across from Cas. The waiter comes and takes their order. Dean, of course, gets a bacon cheeseburger, while Sam, unsurprisingly, gets a salad. The conversation was easy between the four of them. Sam and Dean both try to embarrass the other in front of their respective crush. It earns them both laughter from the two and Dean is taken off his feet when Cas gives a full body laugh from one of Sam's stories about Dean; Dean can't even be angry at Sam for the embarrassing story.

"And Sam," Dean chuckles as he continues a story he was telling, "when I finally got him to watch the star wars movies, that Halloween he dressed as Chewbacca. He comes out of the bathroom with the costume on and I said, _'Sammy, what are you doing? We gotta go! Go get your costume on. I get it, your hair makes you look like a wookie, but come on, man.'_ And he," Dean chuckles dropping his head, his shoulders slightly shaking, "He was so pissed at me."

Sam's smile is wide and he drops his chin to his chest nodding at the memory. "It's true, I wouldn't talk to him for an hour."

Dean looks up, still smiling, and sees Cas' famous confused expression; squinted eyes and tilted head. Dean arches a brow, "Something wrong?"

Cas opens his mouth a little and squints his eyes harder, almost as if he's trying to figure out the world's most puzzling game of sudoku. "I don't understand, what's a wookie?" Everyone simply stares at him with a mock-disgusted expression for a moment longer than Cas is comfortable with, making him fidget a bit. "What?" He asks confused.

Dean leans forward, elbows resting on the table, pointing a hand in his direction and Cas' eyes flick to him. "You're telling me, you've never seen Star Wars?"

"I've never seen them, no." He glances around again and looks back to Dean. "I don't see why that's earned the ostracizing." Cas frowns.

Dean shakes his head leaning back in his booth. "That's just unacceptable," Dean smiles a little adding, "but don't worry, come over to my place tomorrow, I'll educate you properly, and you'll be allowed to join the group once again. You'll leave a new man."

A slow smile works its way onto Cas' face looking into Dean's eyes. "I'm sure I can make it."

"Awesome. You, me, and Sammy, movie marathon. Jess, you're invited too, seeing Sam's cool with that."

"Yeah, of course I'm cool with it." Sam adds with a smile.

They give a time for when they should come over, and then they hang out for a little while longer before heading home for the night.

XXXXX

The next day, Dean is a nervous wreck from the moment he wakes up. It only fully hit him that he invited a, most likely, ridiculously rich actor to his tiny dirty house. So ever since Dean woke up, he has been running around cleaning the house to make it even moderately more acceptable. Sam simply watches from the couch in amusement.

"Dean, the house isn't even that dirty. Why clean it?"

"Because it's filthy, Sammy, now get off your ass and help me."

Of course, Sam continues to sit on the couch and watch him run around. This is the most Sam has seen Dean clean in years, and he's going to allow himself to enjoy the fact that he's doing it because of Cas. He only wishes he was going to be here tonight to see how Dean acts, but Sam knows Dean is probably internally freaking out, and he wants this to go well for his brother, so he speaks up again.

"Dean, he isn't going to care what the house looks like. He's just going to be happy he's here to hang out."

Dean sighs running a hand through his hair, he looks around and lets himself realize that the house is actually pretty clean. He walks over to the living room and plops on the opposite side of it that Sam's on.

Sam leans over to looks at the clock on the microwave and stands up. "Okay, now that you're settled," Sam claps his hands together and makes for the door making Dean sit up stiffly and watch his every move. "You and Cas have fun, Jess and I are going out."

Dean's eyes widen and he stands up abruptly. "You can't. Sam, we had plans."

"And you're a big boy, you can hang out with Cas." When he sees Dean's panic in his eyes, Sam sighs. "Look, this is her free night, we want to go out." Sam gives him a reassuring smile as he pulls on his jacket. "You'll be fine. If anything goes down, I'm sure you have my number." Sam teases and Dean actually checks his phone to make sure he does which makes Sam stifle a laugh. "Good?"

Dean thins his lips waving his phone a bit with a nod.

"Good. Have fun, I'll be back later." And with that, Sam leaves the house.

Dean sighs and looks around the house feeling the urge to start cleaning again simply to give himself something to do, but he represses the urge and slowly sits back down on the edge of the couch.

Dean hasn't been this nervous about someone coming over in ages, not since his first date with Lisa. His mind grids to a halt at that thought. It isn't a date though, so he doesn't know why he's nervous. Although, technically now it could be considered a date seeing how Sam and Jessica aren't going to be here. No! It's not a date. It's just two dudes hanging out watching movies. That's all … not a date.

This relaxes Dean a bit when he realizes he's overreacting, and he's able to sit back on the couch without fidgeting. That is until a knock comes from the door, and all his thoughts come swirling back full force like a punch to his gut.

Dean quickly stands and makes his way over to the door and opens it, not giving himself time to hesitate. Cas stands in the doorway, a smile appears on his face when he sees Dean.

"Hello, Dean."

"Hey, Cas." Dean steps aside and lets Cas come in and take his shoes off. "So," Dean starts. "Sam and Jess bailed."

Cas looks up from taking his shoes off and gives a small surprised look. "Okay." He frowns seeing the look on Dean's face. "You're upset."

Dean's eyes widen and he quickly shakes his head. "No, it's not why you think. I was just told last minute so I ordered pizza for four."

Cas gives a small smile and does his best to cheer Dean up by saying, "Well I'm starving, so I'm sure they won't go to waste."

Dean chuckles and nods for him to follow him into the living room. "I don't think we can polish off four boxes of large pizzas."

Cas' eyes widen for a second before he smiles and taking a seat on the couch while Dean puts in the movie. "That sounds like a challenge, Winchester."

Dean turns around with a sly smile and sits on the other end of the couch. "Maybe I meant it as a challenge, Novak. Whoever eats the most pizza wins," Dean smirks. "But I gotta give you a fair warning. I can put 'em down with the best if them."

Cas only smiles wider. "It's a good thing I don't back down from good competition. What does the winner get?"

Dean drops his head with a small chuckle making Cas squint his eyes. Dean looks up again to meet his eyes then shakes his head and shrugs. "Free beer?"

"What were you going to suggest."

Dean shakes his head. "It could be bad for your career if you get caught when you lose. I don't want to jeopardize anything."

Cas narrows his eyes looking rather determined. "What is it?"

Dean looks into his eyes for a moment longer then decides to tell him. "I was going to say the loser has to go skinny dipping in the lake, but that's something I'd bet with my more rebellious friends."

"I'm in." Cas abruptly says. Dean snaps his head to Cas with wide eyes. "Unless," Cas adds with a teasing smirk. " _You're_ too scared."

Dean barks a laugh, throwing his head back before looking back into Cas' eyes. "Oh, buddy, you're so on, but don't say I didn't warn you."

"I'm not worried." Cas says confidently.

The doorbell rings a few minutes later and Dean gets the pizzas, bringing them into the living room with a two liter of soda and puts them on the coffee table in front of the couch they're both going to be sitting on. Dean then makes a quick trip to the kitchen and grabs two plastic cups and pours them both a glass. After they're settled, Dean starts the movie, both grabbing a slice of pizza.

The both of them end up eating four slices before they had to stop and take a break unless they wanted the buttons on their jeans to pop off. Cas will be able to eat another piece before long. Dean, on the other hand, is cursing himself for getting himself so worked up before Cas showed up. Now that his stomach was twisted with nerves, his stomachs shot, but he'll be damned if he's gonna lose this. Cas said he wanted in on the bet, so Dean will show no mercy. Cas, though, is just as determined.

The movie ends, and they continue the marathon. Dean asks what he thought after every movie, and Cas tells him his thoughts, which were positive. By the time the last movie is playing, Dean and Cas have totaled three pizzas and two slices of the fourth. Dean groans when the credits roll, half-eaten pizza in his hand. He goes to take another bite but shakes his head and throws it back in the box.

Cas smiles seeing him throw the pizza back. "How many did you eat?"

Dean groans and lolls his head onto the back of the couch, hand on his stomach. "Twelve and a half." He rolls his head to look at Cas. "You?" A smug smirk rolls over Cas' features and Dean's eyes widen and he slowly sits up giving a breathy, "No."

"I'm afraid so."

"How many?"

"Fourteen."

Dean lets out a loud groan and lets his head roll back onto the couch, all the while Cas has a triumphant smile unmoving on his face. Dean sighs meeting his eyes once more before closing them again. "Alright, fine, you won." Dean groans and rolls to his side with a quiet, "Fuuuuck."

The next thing that happens is the door opening and Sam's voice coming from the doorway. "Dean, I'm- Oh, hey Cas. Is Dean in the bathroom?"

Cas looks back over his shoulder. "No, he's right here. He ate too much."

Sam looks over the back of the couch and takes in everything. "Holy shit, you two ate three pizzas?"

"We made a bet of who could eat more."

Sam's eyes widen. "And?"

"I won."

Sam gapes over to Dean, who isn't looking at Sam as he's still on his side, and Dean holds up a finger groaning out, "I call a rematch. I wasn't on the top of my game today."

"Yes, but you still have to-" Dean shoots up from where he's curled up on the couch and slaps a hand over Cas' mouth causing everyone to stare in shock. Sam doesn't think he's seen Dean move that fast in a long time.

"Yes, Cas, but some things are meant to stay between us." Dean drops his hand and sits back on the couch, looking back to his brother, who looks curious, but that was bound to happen given Dean just slapped his hand over Cas' mouth and told him to shut his pie hole. "So, Sammy, how was your date you ditched us for?"

"Great." He says albeit skeptically. "Really great, uh, but I have homework I have to do so you two … don't get into any trouble. I don't want to bail you out of jail."

"I can't promise anything for me, but I'm sure you won't have to worry about Cas." Sam huffs a laugh and heads to his room, Dean shouting a, "Have fun." over his shoulder, and just when he's about to say something else to Cas, Cas' phone rings.

Cas reaches for his phone, already looking rather annoyed. He sighs and looks to Dean apologetically. "I'm sorry, I should take this."

Dean stands grabbing the empty pizza boxes and smiles. "No problem." He then heads to the kitchen.

Cas answers the call saying, "Hello?" There's a pause and Cas pinches the bridge of his nose. "It isn't my fault you came to my house uninvited and expected me to be there … No, Michael, I told you I was going out tonight, you just brushed me off … I am not a child anymore, Michael, you don't have to monitor my life." Dean makes his way back into the living room and he can hear Michael shouting something angrily over the phone. Cas sees Dean re-enter the room and quickly cuts his brother off. "I have to go, Michael. Have a good night." He doesn't wait for Michael to respond before he hangs up on him.

"Working with your brother doesn't seem like all sunshine and rainbows." Dean gives a sympathetic smile.

"He has good intentions," Cas sighs.

"But?"

"He does come on a little strong." Immediately after Cas says this, his phone beeps and he looks at the screen.

"That him?"

"Yes, he wants to know who I'm with." Cas pockets his phone looking up to Dean who is giving him a weird look. "What're you're thinking?"

"Well," Dean starts a little hesitantly with a small shrug. "I'm not trying to overstep, but you're an adult, you know what you're doing. On the off chance something bad does happen, you'd have his number if you needed to call."

"Gabriel and I have tried to tell my brother that many times, but Michael doesn't listen to Gabriel since he 'left us'."

"You mean left to make the cafe?"

Cas nods. "Michael told Gabriel he was betraying his family and he was embarrassed to be with us, and that's why he left."

"Michael seems like an asshole."

"Yes, he can come across as such, and family events are tense with them in the same room."

"Remind me to never come over for Christmas." Dean jokes and it earns a chuckle from the other man. After a moment, he sees Cas thinking about something, and on impulse, Dean grabs his jacket and keys. "Get your shoes on, I feel like going for a drive."

Cas quickly stands and gives Dean a confused look, but does as he's told and Dean shouts to Sam that they're heading out. Cas doesn't ask any questions until they've been on the road for a few minutes.

"Where are we heading?"

"Don't know," Dean smiles over to Cas for a quick second. "Just going for a drive, unless you've got somewhere you want to go?"

Cas looks thoughtful for a moment before smiling. "There is one place I'd like to visit again."

Cas tells Dean where to turn and how to get to where he wants to visit, and when they pull into a high school parking lot, Dean is only momentarily confused, thinking maybe they're in the wrong place, but then Cas gets out. Dean does the same and looks through the chain link fence they're standing in front of, and on the other side is a football field.

"I've always wanted to stand on that field," Cas admits.

Dean looks over at him staring at the field longingly and Dean has an overwhelming urge to give Cas what he wants, but the gates are locked. Dean purses his lips then shrugs and asks, "What's stopping you?" while starting to climb the fence.

"The gates are lo- Dean!" Cas whispers harshly. "What are you doing?!"

Dean looks down at Cas as he's nearing the top of the fence, looks back to the fence, then back to Cas innocently. "Climbing the fence."

"You're going to get caught, Dean."

A smirk spreads across his face and he chuckles. "Buddy, this ain't my first rodeo. Now, you coming or not?" Dean reaches the top and Cas hisses for Dean to get down, but Dean jumps to the other side and sticks the landing effortlessly. He turns back to Cas, hands on his hips, a playful smirk on his lips. "I don't know about you, but I'm gonna go stand in the middle of that field."

An array of emotions wash over Cas' face until he settles for disgruntled defeat and starts climbing. It took more effort for Cas, but he finally gets to the top and has no idea where to go from there. He looks to Dean panicked and Dean smiles.

"Put one leg over at a time and jump."

Cas looks at him like he's crazy. "I'm not jumping."

"Come on, I'll catch you if you want."

"I am not jumping on you either."

"Oh come on, all this is coming from the man who bet to go skinny dipping?" Cas narrows his eyes at him and puts a leg over carefully, then another, then he jumps down, stumbling forward a bit only to be caught by Dean. Dean smiles wide at him, their faces a lot closer than intended. Dean notices the distance and his heart skips a beat, but he keeps smiling and pulls away with a pat on Cas' shoulder. "That's more like it. Come on,"

The pair makes their way onto the football field, only stopping when they reach the center. Cas looks around at their surroundings with a sad smile before speaking up.

"I always wanted to know what it felt like to stand here on this field and play as a team."

Dean watches him carefully when he asks, "Why didn't you?"

Cas turns his eyes to meet Dean's. "I wasn't particularly liked by the students in high school."

That confused Dean, and he scrunches his brows together. "Why not? Not to make a big deal of it, but you're Castiel Novak. Even back then everyone knew who you were."

"Yes," Cas nods. "That's precisely why they didn't like me. They felt I got special treatment, so they all got jealous of something that wasn't true. They spread rumors that I didn't actually do my work, my teachers simply gave me such high scores because of my last name. It hurt because I worked very hard for my grades. They just never listened to anything I had to say, and the filed it under excuses.

"Eventually, things escalated and I started to get bullied pretty bad. It ranged from the extreme to the petty teasing about my name being an angel's, but I kept it all quiet from my family. They had tried to have me homeschooled, but they allowed me to go to public school to humor me. At the time, all I ever wanted was to be normal, and at that age, the only thing I could think of that would make me more normal, was going to public school. I should have known better though.

"A group of boys came and beat me up after school one day; it was actually right behind those bleachers." Cas gestures to the metal bleachers. "Thankfully though, Gabriel saw this because he was coming to take me somewhere after school. He figured out that the bullying had been going on for a while, and that ultimately ended my time at this school."

Dean wants to say something, but what does someone say to something like that? "Cas," Dean tries because he can't just say nothing when the man poured his heart out to him like that. "I had no idea."

Cas gives him a small smile. "You wouldn't. I've done well to keep that part of my past hidden from bright lights and flashing cameras, and it's not like those in my school will come out about it either."

"If you've kept it hidden for so long, why tell me?" Dean asks, genuinely confused.

Cas makes sure Dean is looking him in the eye before saying, "Because I trust you, Dean."

Butterflies erupt in Dean's stomach hearing those words. He drops his head a little and he doesn't stop the small smile from showing on his face, but the giddy feeling doesn't last long before Cas is smirking at him deviously.

"The night is still young," Cas says teasingly making Dean grimace. "Not to mention it's perfect temperature for a swim, wouldn't you say?"

"Y'know," Dean starts and points a finger at Cas. "Any bonding moment we had going on right there, completely gone." Dean teases and Cas throws his head back in laughter.

When they get to the lake, they get out of the car and scope the area for any sign of life. When they both give the all clear sign, Dean makes his way to the sand and overlooks the shimmering water. Of all nights to have to do this, it just had to be on one of the most crystal clear, full moon nights. But it doesn't matter, Dean isn't going to back down now. A bet is a bet.

Cas is standing up on the grass leaning against the Impala approximately fifteen feet away. Dean starts to strip off his clothes and Cas can't tear his eyes away, thanking his lucky stars that it's a full moon so he can see Dean's back muscles rippling under his skin as he rips his shirt off. Next is the boots, then Dean whips off his belt dramatically making Cas laugh, but his laughter catches in his throat when Dean starts to teasingly slide his jeans down.

Cas knows Dean is doing this as a joke, but holy hell if it isn't going straight into Cas' late night thoughts bank, and heat flooding south. The only images that are running through Cas' head are of Dean giving him a lap dance, but he quickly shifts his thoughts before he can get himself any harder than he already is, but reality isn't any better because Dean is now gliding his boxers down and kicking them off.

Then, to top it all off, Dean strikes a pose by bringing up both arms and flexing, then extends one arm out. Cas can't stop the laughter from bubbling out of him. Dean then runs into the water enthusiastically, only turning around when the water gets to his hips. Cas straightens up when he's done laughing and see Dean now facing him with a smirk.

Dean then shouts just loud enough for Cas to hear, "You just gonna stand there all night or are you gonna join me, angel?" Cas' breath hitches at the nickname and he feels heat rush south. Moments later he's ripping off his clothes and running into the water hearing Dean shout, "That's what I'm talking about!" with a hearty laugh.

When Cas swims out next to Dean, they're both smiling from ear to ear.

"You're a terrible influence on me." Cas jokes with a laugh.

"But I'm a fun terrible influence."

"Yes, I'm afraid you are."

The two swim around the moonlit water, sometimes splashing each other, other times they float on their backs holding hands. They say it's so they don't get too far apart, but that's an excuse and they both know it. In this moment, it feels like it's only them in the world, and nothing else matters. As the night drags on, they both know they have to head home, but neither of them are willing to break the illusion. So they don't.

Instead, they end up on the little beach where their clothes were abandoned, both now fully dressed, sopping wet, wrapped in a blanket, and they just stare at the stars. For right now, they're going to pretend like nothing else matters, like they're a couple of teens with no reasonabilities, and just bask in the moment. No words are spoken because no words are needed.

They stay there until the sun starts to come up, both of them laughing and sharing stories, only leaving when Cas' alarm goes off in his pocket indicating for him to wake up. In any other moment, Cas would have panicked about not getting any sleep, but right now, he simply laughs because the saying 'Time flies when you're having fun.' has never felt truer.


	9. Chapter 9: Dinner At Castiel's

Just as a warning for anyone who doesn't like this kind of stuff, there is an explicit scene in this chapter, and before you get excited, no, it's not Dean with Cas. It's just Dean.

* * *

 **Chapter 9: Dinner At Castiel's**

Cas didn't wait too long after their little escapade before inviting Sam and Dean over for dinner. He told them Gabriel is holding a small dinner party at Cas' house.

"He's hosting it at your house?"

"Yes, he says it's more convenient since it's bigger than his."

Dean consulted his brother about it to make sure he was free, and when Sam gave him the green light Dean texted Cas to let him know they'd be there tomorrow. Cas responded with a smiling emoji, which Dean thinks is incredibly adorable how much Cas loves his emojis, or, as Cas calls them, emoticons.

Later that day Cas sends Dean a text with another emoji that reminded Cas of Dean, and this has happened a few times now, and every time Dean held himself back, but he risks it this time. It will be less suspicious now that Dean knows what Cas' name actually means. So he decides, why not send it?

{picture of a text message}

Cas: (hamburger emoji) This emoticon reminds me of you.

Dean: It took me a minute, but now I understand. It's cause I'm delicious, isn't it?

Dean: Well I have one that reminds me of you, wanna see it?

Cas: Of course

Dean: (angel emoji) it's an angel. Get it? Since your name is angel of Thursday

Cas: Oh, yes, that makes sense

Little did Dean know that that made Cas a blushing mess for the rest of his day.

The next day comes a lot quicker than usual, but it isn't a beautiful sunny day they were all hoping for. Instead, it's dark, cloudy, and a torrential downpour.

"Dean, where the hell are all the umbrellas?" Sam asks from the hallway closet.

"They should be in there-" Dean hesitates and makes a look of realization. Sam looks over at him and furrows his brows. Dean nods with a smile. "We don't have any."

"How do we not have any umbrellas, Dean?" Sam asks accusingly.

"Benny and I may have made a bet a long time ago to see if we had enough umbrellas if it would work as a parachute." Sam's eyes widen at the ideas running through his head. "So we took them all and strapped them to me and I jumped off the bridge."

"What the hell, Dean?"

"Yeah, I know, it didn't even work," Dean says with a small pout.

"And now we're going to get soaked running out to the car."

"Oh, come on, Sammy, a little water never hurt anybody." Sam narrows his eyes at his brother and Dean rolls his eyes. "Right, kill me later. Right now we gotta scoot boot and boogie."

The brothers waste no time in sprinting to the car and throwing themselves inside. Those few seconds in the rain, even though they ran fast, has them on the verge of soaked. Sam simply looks at Dean unamused and Dean points a finger at him saying, "Don't even say it, Sammy." before starting the car and heading out.

When their destination comes into view and Dean parks the car, he has to take a moment to look the house over. Dean knew Cas' house is big, Cas even said it himself, although less directly, but _damn_.

Dean looks over at Sam with an expectant raise of the brow. "Ready?"

Sam nods and they get out and run up to the house, under the roofed porch and ringing the doorbell. Yet again the few seconds they were out in the storm got them the rest of the way wet. They weren't quite soaked to the bone, but their clothes were dripping.

"In retrospect, maybe ruining all our umbrellas wasn't the best idea."

"You think?"

The door swings open a few seconds later to reveal Cas. Cas' smile falters when he sees the state they're in. "You're soaked."

"Thank you, captain obvious." Dean teases. Cas lets them in, Sam closing the door behind them.

"Follow me, I can lend you some clothes if you'd like."

"That would be amazing." Dean smiles and Cas leads them up the stairs to his room. When they enter the room, Dean looks around at his surroundings as Cas immediately goes to his closet. His room looks nice. Simple, but nice.

"Here," Cas' voice sounds from behind him making him spin around. Cas is holding out clothes for the brothers. "They should fit. I had a pair of Michael's old clothes that should fit you, Sam.

"You've got a nice house." Dean says as he starts to strip, the conversation keeping Cas in the room, so he turns his back on them.

"Thank you, it was my parent's house, but they gave it to me a few years ago. I have to admit though I would be much more comfortable in a smaller home."

Cas' phone starts to sing in his back pocket so he pulls it out and sees who it is. Sees Gabriel's name and tells the brothers he'll be right back before going into the hall and answering the call.

"Gabriel, where are you?"

"Ah, yeah, about that, little brother. I'm not coming, neither is anyone else. Samerella and Dean-o are there though, that's all that matters."

Cas narrows his eyes at the wall. "Do not tell me this was a prank."

"Okay, so I won't tell you." Gabriel laughs lightheartedly.

"You are insatiable."

"Yeah, yeah, but you love me. Hey, don't go making any bets with Dean about who can eat more, I'm still coming in just gonna be late."

Cas' face flushes a light shade of pink. "How did you hear about that?"

"How do you think, kiddo? Sam texted me asking if I knew where you two got off to when Dean didn't come back that night. Castiel, he texted me at three in the morning. _Three_. And he didn't stop until I answered." Gabriel groans over the phone. "Next time you want to get laid, tell Sam you two aren't coming back."

Cas' eyes fly wide open. "It wasn't like that, and you know it!" Gabriel barks a laugh and then all of a sudden there are horns honking on Gabriel's side of the line and a loud crack of thunder. Cas frowns thinning his lips. "Are you okay? I'm hearing a lot of horns on your end."

"Yeah, I'm good, the road is just starting to floor and it's hell's highway over here, but don't worry I should be there soon … ish. And before you tell me not to come if it's that bad, I'm already halfway there."

"Alright," Cas sighs running a hand through his hair and glancing out the window at the end of the hall, it's starting to get a little darker out, but that could just be because darker clouds are rolling in. "be safe, Gabriel. I'll make sure to save you some food."

"Thanks, Cassie. Give the boys kisses for me."

They hang up and Dean's voice comes from behind him. "Gabriel okay?"

Cas turns around and comes to a halt seeing Dean in his clothes because damn Cas could get used to seeing Dean wearing his clothes. Cas quickly clears his throat and nods before his mind can drift any further down that road. "Yes, he's okay. The roads are flooding though so he's going to be late. Although it appears this was another one of Gabriel's pranks. A rather poor prank, but a prank nonetheless."

Sam arches a brow. "What was the prank?"

"To say we were having a dinner party, but only you two were actually invited." Cas scrunches his brows together and squints his eyes a little. "Granted I was planning on inviting you two over for dinner sometime anyway, so I'm not quite sure I understand the prank aspect of it."

Dean claps his hands together with a smile. "Well, in that case, how about we get started making dinner." Cas looks up with a smile and nods.

The three of them all start getting the ingredients and pans out, and even though Sam and Cas both had good intentions of helping with the cooking, Dean was the one who shoved them to cutting things up because frankly, they aren't the best cooks.

Dean looks up when he sees someone else walk into the kitchen. "Convenient timing, we just finished up."

Gabriel smiles wide as he walks over to them. "Lucky me, looks like I don't have to do anything."

"You're on dish duty," Cas says, effectively making Gabriel deflate.

The older Novak doesn't stay deflated long though before he notices Sam and Dean wearing Cas' clothes. He arches a brow. "Do I have to wear your clothes too, or what's going on?"

"We're wearing Cas' clothes because I have an idiot for a brother," Sam says, still a little bitter over it.

"Hey," Dean gives a mock hurt look. "it was a long time ago." They all grab their plates and make their way into the dining room taking their seats.

"What did you do?" Cas asks curiously.

"I may have broken all our umbrellas."

"He wanted to try and fly." Sam adds and Cas' eyes widen.

"Okay, no, I didn't want to _fly_. I wanted to see if the umbrellas could work as a parachute."

Gabriel barks a laugh while Cas just stares in shock. "Did it work?"

Dean chuckles and shakes his head. "No, it got me a broken leg."

"Wait, that's how you broke your leg?"

Dean nods looking at his plate and grabbing the burger taking a bite. Everyone else following his lead and Cas barely holds back a moan as the flavor washes over his tongue. He savors it before swallowing to speak again.

"This is really good, Dean. I had no idea you were such a good cook."

Dean smiles and the butterflies in his stomach stir. "Cooking is the one thing I'm really good at. Someone had to keep this sasquatch fed."

Before anyone could reply, all of their phones start to vibrate and a warning sound goes off. Dean furrows his brows and checks what's going on. There is a flood warning on his phone's screen.

"The roads are flooded." Cas states looking up and meeting Dean's eyes. Cas opens his mouth to say something, hesitates, then proceeds. "Would you like to stay here for the night so you don't have to drive in this?"

Dean knows that he would be fine driving home, but the thought of staying longer with Cas is far too tempting. Not to mention he's wearing Cas' clothes so he should wait until his clothes are dry to leave. Plus, if they don't _have_ to get soaked again, then he isn't going to leave. Then it connects with him that he isn't just making the decision for himself, Sam might have something he has to do. He glances over to his brother. "You have anything you really need back at the house?"

Dean sees the split second of hesitation before Sam shakes his head. "No,"

Dean can feel it in his gut that Sam is lying, but for once he's not going to push. "Alright, then if it's not too much trouble, we'll stay." Better safe than sorry, right?

After they finish up their dinner, the four of them decide to watch a movie. They all make their way into the living room and they scan the, rather sparse, selection. Gabriel is the first to pull out a movie.

"Cassie, you never watched the movie I got you."

Cas narrows his eyes at his brother but stops when Dean looks at the movie and his face lights up. "Whoa, Cas, you've got _The Orphanage_? We've got to watch it." Dean turns to Cas with a wide smile. "You good with that?"

Cas opens his mouth but quickly closes it, placing a smile in place and nods. He only glares at Gabriel when his brother snickers.

Sam sits on one couch and Gabriel quickly swoops in to take the other spot, and unless Dean wanted to sit between the two, he is left with sitting on the loveseat with Cas. Which he didn't mind at all, so he sits beside Cas, leaning comfortably on the armrest, his one arm resting along the back of the couch.

The movie they picked is a horror movie, and to Dean's surprise, he sees Cas staring at the screen looking like he wants to run away. In one scene there is a jump scare and Cas nearly jumps out of his skin. Dean wants so badly to wrap his arm around him, his arm is already so close, but he that probably wouldn't go over very well. Instead, he rests his knee against Cas' and Cas takes to it immediately, scooting closer to Dean so their thighs are pressing together. Cas doesn't tear his eyes from the screen, but he looks slightly less like a frightened puppy.

That is until another jump scare comes on and Cas jumps and grabs Dean's knee in a kung-fu grip. Dean can't help but smile, but repressing the chuckle is a different story. He bites his bottom lip trying to stop it, and finally, the urge to laugh is squashed, but the smile won't leave his face.

When the movie finally ends Cas doesn't move so their thighs aren't pressing against each other, and Dean doesn't mind at all.

"I gotta ask, Cas," Dean starts making Cas turn his head in his direction. "If you were scared of horror movies, why'd you agree to watch it?"

A light pink blush crosses his cheeks and he looks away. "I thought I'd be able to handle it, plus you all seemed so excited about it."

"Wait," Dean looks to Gabriel narrowing his eyes. "You knew he didn't like horror movies, didn't you?"

Gabriel holds his hands up in defense and hides behind Sam who tries to get out of the way, not wanting to get in the line of fire. Gabriel then peeks his head around Sam saying, "Whoa, hey, no need for the daggers there. If Cassie didn't want to watch it all he had to do was say no." Gabriel looks at the clock hanging on the wall. "I don't know about you guys but I'm gonna hit the hay, busy day tomorrow." Gabriel makes his way to the stairs shouting over his shoulder, "Don't stay up too late kids."

Before anyone else can say anything, Sam turns away yawning. "Sorry, I had a hectic day today."

"That's alright; we can head to bed now too. Follow me. I have some new toothbrushes you can have." Cas leads them back the hall to the bathroom and gets them both a toothbrush.

"Thanks, Cas."

"Of course," Cas smiles, "You two have the first two rooms on the left at the top of the stairs when you're done." Cas then leaves them alone to get ready for bed.

The brothers get ready in relative silence and then head up to the rooms that Cas told them were theirs. Dean takes the room further down the hall saying a quiet goodnight to Sam before heading in. He closes the door most of the way and walks over to the bed seeing folded up pajamas on the corner of the bed. Dean smiles, he appreciates the offer, but he hasn't been able to sleep comfortably in more than his boxers in years, so he sets them on the nightstand by the bed and strips to his boxers, getting in the bed.

The bed is so soft, Dean feels like he's in heaven. He lays on his back and closes his eyes, taking in a deep breath. The room smells nice. It smells like Cas, which makes perfect sense seeing how Dean is in his house. That's when Dean feels a familiar twitch in his stomach. He knows he shouldn't, he really, really shouldn't, but thinking that doesn't stop the heat from pooling to his groin.

Dean groans in annoyance, trying to ignore it, but it's no use, it's all he can think about, and he's not going to get to sleep without taking care of it. So he reaches a hand down and palms himself through his boxers as he breathes in Cas' scent.

Growing quickly annoyed at the fabric of his boxers, he quickly pushes them down. He continues to touch himself for a little while before he starts to feel an urge bubble in his stomach for the first time in a long time. He brings his hand up to his lips and hesitates before licking them. When he deems them to be slick enough, he brings them down to his entrance, running a finger over the muscle. After a second he gently pushes in one finger to the first knuckle and lets out a shaky breath.

Cas' scent on the pillows has a calming effect on him but also serves to make him more aroused. He works himself open to slide the second finger in and scissor himself. His fingers brush against his prostate and he bites back a moan arching his back imagining that Cas is the one doing this to him. He imagines him naked hovering over him, looking at him with those powerful blue eyes that send shivers down his spine.

Dean knows he should be feeling bad about doing this, he really does, but that rational part of his brain that is usually there to say 'This isn't right, we should stop.' isn't there. Instead, they are replaced with 'Fuck it, only I will know what I'm doing right now.'

He brings his other hand to his cock and continues to pump himself a little sloppily. Thankfully he doesn't have to keep at it for too long before he's coming into his hand and on his stomach.

He keeps his eyes closed and catches his breath for a few seconds before opening his eyes and whispering to himself, "What did I just do…" his rational thoughts flooding his head making him feel guilty. Not to mention he hates himself for loving it so much. He shouldn't like being finger fucked. He especially isn't supposed to get so turned on by the thought of his fingers being Cas' dick in his ass.

He is not supposed to think of Cas that way when the man let him stay in his house out of The kindness of his heart, and Dean just jacked off to the thought of him. What the hell is wrong with him?!

Dean groans and decides it's a good idea to clean himself up, so he grabs the pajama bottoms and his underwear and slides them on. He makes sure to be as quiet as he can as he walks down the stairs and into the bathroom. He cleans himself off then glares at himself in the mirror before leaving the room. As he makes his way to the stairs he stops when he sees Cas sitting on the couch reading a book.

"Can't sleep?" Dean asks making Cas jump, looking wide eyed up at Dean.

Cas sighs when he sees it's Dean and gently closes his book, resting it on his lap. "I'm afraid not."

Dean smiles a little and comes around the couch, taking a seat next to him. "That movie really messed you up, didn't it?"

Cas rubs the back of his neck sheepishly. "I have a weak constitution when it comes to scary movies." Cas gives a small chuckle. "I was hoping I'd be able to play it off longer than I did."

"Don't worry, I'll protect you from the monsters, Cas." Dean cracks a wider smile at him when Cas blushes. The both of them sit in a comfortable silence for a few seconds before Cas speaks again.

"Why're you up? I don't think it was because of the movie."

"Oh," Dean jabs a thumb back in the direction of the bathroom. "I, uh, had to go to the bathroom." Cas nods and Dean pulls his bottom lip between his teeth debating how he can help Cas get to sleep. "Hey, uh, is there anything I can do to help you sleep? I mean, it was partially my fault for the movie."

"It wasn't your fault, Dean." Cas frowns, not wanting Dean to blame himself for Cas' lack of sleep.

Dean drops his eyes to the book in Cas' hands and arches a brow. "What're you reading?"

Cas' eyes widen and he looks down then back up with an almost shy smile. "It's silly," Cas holds it up and shows Dean the cover. "But I find it relaxing."

"Charlotte's Web?" Dean smiles wide, "I used to read it to Sam as a bedtime story all the time. I could recite the book without it in front of me." He holds out a hand for the book. "Can I see it?"

Cas nods and hands it over to Dean. Dean takes it and cracks it open, the spine not making any noises when he does, indicating it's been well loved over the years. When his eyes land on the first page he can't help but smile and read them aloud. "'Where's Papa going with that ax?' asked Fern to her mother as they were sitting at the table for breakfast." Dean sees Cas smile out of the corner of his eye so he continues to read it.

Ten minutes later, Dean glances over to Cas when he feels something fall on his shoulder. Cas fell asleep. Dean quietly closes the book and sets it on the coffee table before carefully situating himself and Cas so they can sleep on the couch comfortably together. When Dean settles them back, Cas snuggles himself into Dean's chest and Dean pulls the blanket from the back of the couch over them both.

"Goodnight, Cas." Dean gently kisses the top of Cas' head before closing his eyes to sleep.

XXXXX

Dean groans as he starts to wake up, but the smell of coffee and bacon wakes him up enough to opens his eyes and take in his surroundings. He squints and furrows his brows as he groggily sits up. Why is he in the living- oh. He feels his cheeks slightly heat up remembering everything he did last night. He goes to stand up but pauses when he sees his clothes neatly folded on the coffee table. Grabbing them he makes his way to the bathroom and gets ready for the day, trying to tell himself to not act weird around Cas because he was stupid and embarrassed about last night.

Dean makes his way into the kitchen where Cas is leaning against the counter with a mug of coffee. He looks up and smiles at him. "Would you like some coffee, eggs, and bacon?"

"Yeah, uh, thanks." Cas nods and gets him his coffee and food. Dean takes it with a nods and he eats it quietly at the center island.

"Are you okay?"

Dean jolts at Cas' question, looking up to meet his eyes. He thought he was acting normal. "Yeah, I'm fine. Why?"

"You just looked like you had something bothering you."

"That's just my morning face." Dean laughs trying to make light of it. "I'm fine, really."

When Cas nods and turns around to get more coffee, Dean breates himself. He's the only one who knows what he did last night. He needs to stop acting weird or else Cas is going to end up finding out, and god he hates himself for kind of getting turned on again by the thought.

He clears his throat and speaks to get his mind off it. "So, do I need to go kick my kid brother's ass outta bed?"

Cas turns back around with a smile. "No, he's out for a run. He said he'd be right back, he just didn't want to mess up his running schedule."

Dean pauses mid-sip and lowers his glass with scrunched brows, one brow arching in thought. Since when did Sam start running?

"Is something wrong?"

"Huh?" Dean snaps out of it meeting his eyes. "Oh, no, it's nothing." It's at this moment that Sam decides to show back up, making his way into the kitchen. Dean arched a quizzical brow at his brother. "Running?"

Sam nods his thanks to Cas as he hands him a cup of coffee. "Yeah, Dean, running. I just started not too long ago. I want to get into a habit." Sam pauses and sees Dean turning up his nose at him. "It's good for you, Dean, you should come with me sometime."

"Oh, no, I'm good relaxing here with my bacon and having a lovely morning with my buddy Cas here, thank you very much."

Sam huffs a laugh. "Whatever you say, but when I'm 80 and running laps around you you're going to wish you were me."

"Dude," Dean scoffs, "When I'm 80 I'm gonna be just fine with my ass in a rocking chair on my front porch."

Cas smiles at the brothers, taking another sip of his coffee. He could get used to having mornings like this.

Their morning rolls by smoothly after this. Sam and Dean making light hearted bickering, Gabriel eventually stumbling down the steps following his nose to eat before leaving, and Cas calmly finishing his coffee. Eventually Sam and Dean have to leave and Cas sees them to the door.

"It was nice to have you both here, thank you for coming." Cas smiles at them.

"We had a good time here, thanks for the invite, Cas." Sam says putting his shoes on and opens the door waiting for Dean.

"We'll see you around." Dean smiles and Cas nods. They say their final goodbyes and the brothers go out to the car and get in.

"I saw you fell asleep on the couch with Cas last night." Dean looks over to his brother before looking back forward, his hands on the wheel. "I know you're scared you'd hurt him, but Dean, seeing you last night and this morning, I really don't think you have anything to worry about."

Dean sighs. "I'm gonna do it," Sam's eyes widen. "Later, cause it would be weird to ask him after we just spent the night at his house."

Sam rolls his eyes. "You're just using excuses, if you're going to do it, do it."

Dean knows he's being a chickenshit, but can you blame him? He puts the keys in the ignition and starts her up, but doesn't move any further from there. He drums his fingers on the wheel, then quickly opens his door and makes his way up to Cas' house, knocking on the door before he can lose his nerve.

The door opens a few seconds later revealing a surprised looking Cas. "Dean,"

Dean says hurriedly, "Would you like to get dinner … sometime … with me … maybe?"

A slow smile spreads across Cas' face. "I would love to, Dean."

Dean lets out a breath he didn't know he was holding. "Awesome. Okay, I, uh, will text you then."

"Alright." Cas' smile is contagious and Dean can't stop from smiling as well as he backs up and makes his way to the car again. When he gets in he looks back and sees Cas standing there with his smile, leaning on the doorframe. Cas waves bye as they pull back and they do the same.

Sam doesn't say anything, but it's obvious what happened by the fact that Dean is on cloud nine. Not to mention he couldn't wipe that smile off his face if he tried. Sam is just happy to finally see Dean so happy again.

XXXXX

 **Castiel Novak Finally Gone Off The Market?**

Actor Castiel Novak announced in an interview today that he has in fact found somebody and is currently pursuing a relationship with them, but the thing nobody was expecting was for him to come out as gay. Here is the clip from the interview where he admits it:

 **Interviewer:** So, Castiel, there have been rumors going around about you.

 **Castiel:** Yes, there always seems to be something floating around. People are very dedicated to find something out about me that they didn't already know.

 **Interviewer:** Yes, that is true, but this rumor isn't something we have heard about you before in such a serious tone. Is it true that you are actually in a relationship now?

 **Castiel:** Yes that's true.

 **Interviewer:** What made you finally decide to find yourself a girlfriend?

 **Castiel:** I didn't necessarily wake up one day and think 'Today is the day I'm going to start dating'. I just met him on coincidence and it played out from there.

 **Interviewer:** Wait, did you say _him_?

 **Castiel:** Yes, he is a man.

 **Interviewer:** So this is your way of coming out?

 **Castiel:** I was never hiding, everyone simply assumed that I was only into women and I never felt a reason to mention otherwise. People simply shouldn't assume everyone is straight.

 **Interviewer:** How do you think coming out as gay is going to affect your fans?

 **Castiel:** I don't think it will affect them other than a bit of shock. I don't see why it would cause them to like me any less, unless, of course, they're homophobic. But gay isn't the correct term, I don't like people because of their gender. I like people because of personality.

 **Interviewer:** If you're not gay, or straight, what would you identify as?

 **Castiel:** Human.

 **Interviewer:** No, I meant …

 **Castiel:** I understood what you meant, and I don't see a reason to have to identify as a specific thing. If I do, and I, for whatever reason, decide to contradict it in the future, then it will cause an issue to everyone else. So I am simply human.

XXXXX

{picture of that math meme trying to figure something out}

Caption: When someone you weren't expecting to be gay/bi, comes out and all of a sudden you start realizing everything they've done and you're trying to figure out how you never saw it coming.

I mean, really, Cas though. I feel so stupid.

Comments · Order by **Oldest to Newest**

 **Cassie Castiel** ·5 hours ago

Okay but Castiel said he isn't gay. He says he doesn't want to identify as anything other than human. Honestly I understand what he's saying. People throw fits about bisexual people all the time. Say he ends up marrying a girl, everyone would say "Oh so you're really straight and you just wanted the publicity?" or he marries a man "Oh, so you really are gay and just didn't want to come out completely?"

 **Harold Green** ·5 hours ago

I don't understand all this hype about him being "bisexual", seriously he's just being greedy, pick one. He is just lookin for an excuse to be able to hit on everyone. I don't want no boy makin a move on me just cuz he thinks his sexuality makes it ok

 **Death_is_my_homie** · 5 hours ago

I forgot there are people like Harold Green out there. Shallow assholes that won't take their head out of their ass long enough to see how the world is now. People are unbelievable. If you knew Castiel AT ALL then you would know he isn't like that. And trust me, Castiel wouldn't be the only one who would never hit on the likes of you. Women probably avoid you too with an attitude like that.

 **CasCas Novak** · 4 hours ago

Guys, what does it matter who Castiel prefers, he is still the same old Castiel we know and love, he hasn't changed. He makes heart eyes with a man across the room? Good for him, go get 'em tiger. Got an eye for a lady? That's great too, have fun! This is Cas. If anyone thinks he would hit on them out of the blue they're crazy. Cas is probably one of those people who asks if flirting is okay before he does it. Cas' flirting is probably so subtle you wouldn't even know he's trying to flirt. He wouldn't hurt a fly.


	10. Chapter 10: Cat's Out

Date time! This is more of a fluffy chapter, so those of you who like that kind of stuff will hopefully enjoy it.

* * *

 **Chapter 10: Cats Out**

The state of Dean's room can be described as one thing, a war zone. He has successfully gone through his closet twice, throwing clothes he was going to wear, then deciding they weren't good enough, off his bed and onto the floor. Dean never thought he'd be one of those people that did this before a date, but he's a mess.

Sure he's hung out with Cas at a restaurant before, but that was different. They didn't sit down and eat with each other, and Dean didn't have the pressure of the word date hanging over his head to not screw up. Before if he screwed up, he would still be Cas' friend. Although, if he screws it up this time, Cas wouldn't want to still be his friend, would he? Typically if a date goes south then they part ways, never to speak to each other again. Dean doesn't want that.

A knock sounds from Dean's door followed by his brother's voice. "Dean? You okay?" The door opens and Sam's head peaks into the room, his eyes widening when he sees the mess Dean made. He pushes the door open the rest of the way and steps in, looking at Dean. "What're you doing?"

Dean looks at his brother exasperatedly. "Sammy, I've got nothing good to wear." Dean holds up a sweater. "I can't believe you ever let me leave the house with this monstrosity on." Dean throws it on the ground picking up another shirt. "And this looks like it's been through a war." Throws it on the ground as well and picks up a bunch of other shirts. "They're all plaid and band-tees! I can't wear that on a date!"

Sam's eyes widen and he whispers a quiet, "Wow," He clears his throat holding up his hands trying to defuse his brother. "Okay, Dean, calm down. Cas isn't going to care what you wea-"

"I care!"

"Okay, okay, just," Sam picks up a plaid shirt and furrows his brows holding it up. "What's wrong with plaid?"

"Sammy, if you're not going to help then you need to leave."

Sam gives Dean an are-you-kidding-me look and sets the shirt on the bed. "Dean, I am trying to help." Dean turns away, eyes scanning the floor, running his hands through his hair and muttering something to himself. Sam thins his lips and nods. "Okay, Dean, you stay here, I'll be right back." He quickly turns and leaves, pulling out his phone and calling Charlie's number. This calls for drastic measures.

"Hello?" She answers.

"Charlie, we've got a code rainbow 13-10. I need your assistance."

"I'll be right there."

Not ten minutes later, Charlie shows up and Sam immediately lets her in and takes her up to Dean's room. She opens the door and her eyes widen seeing the mess and Dean saying something about calling the date off.

Charlie glances back to Sam. "You did the right thing calling me." She looks back to Dean who is now looking over at the two with furrowed brows. "Alright, Dean, let's get you something to wear."

Dean glares at Sam. "You called Charlie?"

"Dean, you weren't giving me much choice. Now be quiet and let Charlie work her magic, you're not calling this date off after everything we've been through."

Dean arches a brow at the use of the word 'we', but he lets it go since Sam leaves the room so Charlie can get to work. Dean turns to Charlie with a sigh, running a hand through his hair. "Charlie, you don't have t-"

"Shut up, and sit down I'm helping." Dean's eyes widen and he sits on his bed. "Tell me what the problem is. I see quite a few things you could wear that would look great on you."

Dean sighs rubbing a hand over his face with a small groan. "I don't know, Charlie. Nothing just seems right."

She thins her lips and looks around at her options. "If you simply can't decide, I'm going to pick an outfit and if Sam thinks it's good then you don't get to change." Dean looks like he's about to argue, but Charlie narrows her eyes at him and he shuts his mouth. She smiles and nods. "Good, now let's see what you've got."

It takes her approximately three minutes to piece together an outfit for Dean, then she's shoving him out of the room and down the stairs to the living room where Sam is at. She stands beside Dean and puts her hands on her hips.

"How's it look, Sam? Be honest."

Sam turns his attention to the pair and smiles. "It's great."

Charlie beams over at Dean and pats him on the arm. "You've got nothing to worry about now. You and Cas have hung out multiple times before now, so it should be a slice of pie."

"It's a piece of cake." Dean corrects with a fond smile.

Charlie playfully punches him in the arm with a wide smile. "That's the spirit! Go get 'em, tiger!"

Dean nods and makes his way to the door getting ready then leaves, shouting over his shoulder, "See ya, Sammy, Charlie." Before closing the door and getting into the car. He forces himself to calm down on the drive there. Charlie is right, he's done this before, the only thing that's new is that they're calling it a date. Dean was just getting himself worked up, all he has to do is be himself.

When he pulls into Cas' driveway he's completely calm, only getting butterflies when he sees Cas come out the door. He can't stop the smile from spreading across his face when he meets Cas' eyes through the glass, Cas smiling back just as wide.

Cas opens the passenger side door and slides in with a, "Hello, Dean."

In which Dean responds with his usual, "Hey, Cas."

"So," Cas starts, "Where are planning on taking me?"

Dean smiles over at him and then starts backing out of the driveway. "Typically for first dates, I take them to a fancy restaurant, but I decided to switch it up." Dean gives a quick glance to Cas to see him staring at him. "How do you feel about food trucks?"

Dean's heart flutters when Cas' smile widens. "I love them."

"Awesome."

When they get to the place Dean had in mind, some darker clouds are starting to roll closer form the distance. Dean glares at them as if daring them to rain on his date. The two make their way over to the food truck and order their food, each of them paying for their own meal. Although if Dean would have had it his way, he would have paid for them both seeing he asked Cas out, but Cas wasn't having any of that.

After they get their food they make their way over to a bench in the park right next to the truck and sit down. Dean bites into it and hums in appreciation then looks expectantly over at Cas as he bites into his own. Cas closes his eyes and savors the flavor, and when he opens them again he sees Dean staring at him.

"You like it?"

Cas swallows and nods. "It's very good. Have you been here before?"

"A few times. I'd stop here when I would go and visit Sam at school for lunch."

They talk about little things while they finish up their food, laughing when the other one says something funny, both of them trying to commit the other's laugh to memory. The way Dean throws his head back and belts out a heartwarming laugh when he finds something to be particularly hilarious. The way his eyes crinkle at the sides and his body shakes with laughter. The way Cas will drop his head forward and try to hide his laugh, but he always fails and will shake his head and turn his head towards Dean, eyes crinkled, a wide crooked smile plastered across his face, a playfulness in his eyes that makes Dean's heart sputter with affection.

Once they finish their food, Dean sees a group of adult men playing a game of soccer in the giant field in front of them. Dean lights up and starts to feel excited as he turns to Cas, trying not to look too excited so he doesn't pressure Cas into saying yes.

"Hey, Cas, want to go see if they'll let us join their game?"

Cas looks over to where Dean had been staring and sees some men playing an aggressive game of soccer. Part of him starts to get excited, but the other half of him knows how bad he is at sports. He bites at bottom lip hesitantly saying, "I'm not very good at soccer,"

Dean presses his lips into a thin line quickly before leaning back and shrugging with a smile trying not to appear disappointed. "That's alright, we don't have to."

Cas tears his eyes from the soccer players over to Dean and sees he's trying to look relaxed for Cas' sake, but he can tell he really wants to play. Cas forces himself to gather the courage to not care how bad he looks playing the sport as long as he can see Dean having a good time. "But I'm willing to try."

Dean lights up like a lighthouse and looks over to Cas. "Really?"

Cas smiles widely at how Dean looks like a kid in a candy store. He'd give anything to see Dean look like this. "Of course, I've always wanted to try and play a sport."

Dean beams and stands up, Cas following his eager boy- his date over to the group of men. They stop a few feet from the group and they all turn to the pair.

"We just saw you guys starting a game and wanted to come over and ask if there was room for two more players," Dean says confidently.

The men all look at one another then beam over to the pair welcoming them with open arms. Cas and Dean end up on separate teams, and Dean plans on going easy for Cas since he seems so nervous. When they start the game, Dean is quick to steal the ball from the other team and try to go to the other net. He gets surrounded and kicks it to one of his teammates.

Cas is hanging near the rear watching everyone like a hawk, occasionally trying to join in and take the ball, but someone would always take it from him. Little did they know he wanted them to steal the ball so Cas could study how they did it so he can replicate it. He slowly starts to put what he's learning to use and soon Cas is feeling much more comfortable with the sport and is ready to steal the ball. He sees Dean running down the field with the ball and Cas focuses in and catches up to Dean.

Dean doesn't even see it coming when Cas swoops in and swiftly steals it from Dean, almost effortlessly and Cas' team cheers. Dean snaps his head back to Cas' back with wide eyes, then a wide smirk slowly crosses his face and he knows he doesn't have to hold back anymore. It's on.

Cas ends up earning his head three points and Dean earns four, but Cas seen evens it out in an unexpected way, he uses his head. That has Dean laughing out loud and clapping Cas on the shoulder. Cas smiles over at Dean and then all of a sudden a raindrop plops itself on his cheek. Dean looks over at him when Cas holds out his hands, palms up and staring up at the sky. Dean looks up and immediately gets pelted in the middle of the forehead with a raindrop.

Dean curses under his breath and looks over at Cas about to ask if he wants to head out, but Cas starts to laugh. Dean smiles seeing Cas look like he's really enjoying himself and Dean no longer cares about getting wet anymore.

They all continue to play their game of soccer, the ground slowly becoming a muddy mess. Mud sloshes up onto the hem of their pants and up their legs, the rain plastering their hair to their heads. Dean keeps running a hand through his hair to push it out of his eyes. He runs up beside Cas since he has the ball and he goes to try and take it, but he fails and instead, he starts to fall. Cas notices and tries to catch him, but it only results in both of them falling into a puddle of mud, along with most of the other men around them. Dean's shoulders start to shake and Cas looks him over worriedly.

"Dean, are you hurt?"

Dean throws his head back and startles Cas with a boisterous laugh, but once Cas is reassured that Dean is, in fact, not hurt, he starts to laugh along with him and the other men. Dean's laughter slows and he looks over at Cas to see him still laughing, his eyes closed. They're a lot closer than Dean had thought, their legs tangled together in the pile of bodies. Dean's heart soars hearing Cas' laugh so close he can almost feel it in his own chest.

Cas opens his eyes soon, coming down from his laughing fit and meets Dean's gaze. Dean's eyes flick up form Cas' lips and he starts to blush as if getting caught doing something bad. Cas tries to even out his breathing from running around and he brings up a hand to Dean's cheek to wipes off some mud, then slowly snakes it around to the back of Dean's neck and starts to lean in. He pauses when he feels a light brush of Dean's lips, pulls back a little and then goes back in, fully connecting their lips. Dean pushes into the kiss, running his hand up to Cas' hair and pulls him closer.

That's when the men that they were playing soccer with all start to whistle and holler at them, and this makes the pair remember they're not alone. Cas pulls back looking into Dean's eyes and Dean slowly starts to smile.

"I don't usually kiss on the first date," Cas says with a gentle smile lightly squeezing the back of Dean's neck.

"But you made an exception for me."

"You're different."

Dean has another slow smile spread across his face and he starts to chuckle. He closes his eyes and drops his head, looking back up when he says, "You just Ryan Gosling'ed me."

Cas smiles wide and pulls Dean back in for another quick kiss, needing to feel his lips on his again. "I didn't know you were a fan of _The Notebook_."

Dean shrugs. "Guilty pleasure." It's at this moment that a loud crack of thunder booms across the storm-ridden sky followed by quick flashes of lightning. Dean starts to stand, holding out a hand to Cas saying, "That's our queue." Cas takes his offered hand and Dean smiles back to the men. "Thanks for letting us play with you guys, but we're gonna head out now."

They say their goodbyes and make their way to the Impala, only when she comes into view does Dean realize they're going to cover her in mud, and he doesn't have any blankets in the trunk. He internally cringes thinking about mud getting in her seats, but sucks it up and tells himself that he'll clean her up good tomorrow. They get in and Dean drives Cas home and when he pulls up into the driveway he looks over to Cas with a smile.

"I had a great time today, Cas."

"Me too." Cas smiles and then Dean is leaning in for one more kiss before Cas has to leave. Dean pulls back and Cas can't stop himself from leaning back in and reclaiming his lips. He just can't get enough of feeling Dean's lips on his. This time when Cas pulls back he goes for the door. "I'll text you."

"Alright, see ya, Cas."

"Goodbye, Dean." and Cas gets out into the pouring rain and casually walks up to his door. Dean waits for him to get inside before he pulls out and heads home.

When Dean pulls into his driveway he sits there in the Impala for a few more seconds after he shuts her off to sigh contentedly, then he pulls himself together so he's not swooning when he gets inside. Upon opening the door he hears Charlie's voice coming from the living room talking to Sam. Dean takes off his boots and mud-soaked socks and makes his way to the arch of the living room.

Charlie's eyes snap to him with a smile that quickly drops and she gasps covering her mouth. "Oh my God, Dean, what happened?"

Sam looks over and his eyes nearly pop out of his head seeing the mud monster Dean became. "Dean, what…"

Dean does everything in his power to not smile like an idiot, but it's no use. Images of their date come rushing back to his mind and he starts to laugh and smile like a schoolgirl. He sees a fond expression pass both their faces and Dean fills them in on everything that happened, telling them everything since he secretly wants to relive it. When he tells them about his "The Notebook" moment, Charlie squeals and goes to hug him then stops abruptly remembering he looks like he just crawled out of a swamp. So instead he settles for jumping up and down excitedly in front of Dean.

"You've seen The Notebook?" Sam questions and smiles teasingly at his brother who gives him the stink eye. Sam stands up with a laugh and pats him on the shoulder. "See, Dean, I told you there was nothing to worry about." Sam looks him over and puts his other hand on Dean's other shoulder and turns him around and gives a small shove to the stairs. "I'm happy for you and everything, but you need a shower."

Dean laughs and turns back towards them. "Yeah, yeah, I have to give my dear friend a hug goodbye though." Dean holds out his arm and walks towards Charlie.

"Don't you dare, Winchester!" He lunges at her and she runs to the door. "Good luck, Sam. Bye, Dean!" She quickly runs out the door before Dean can catch her in his muddy grasp. Dean starts to laugh and he turns to Sam who's shaking his head with a smile. That's when Dean sneezes.

Sam's eyes go wide staring at Dean who is blinking away his watering eyes from the sneeze. "Oh no," Sam mutters.

Dean waves a hand at Sam to tell him it's fine. "It's just a sneeze, Samm-" He interrupts himself with another sneeze and whispers to himself, "Fuck,"

Sam points up the stairs with a no bullshit tolerating expressing. "Hot shower, now."

"Yeah, yeah, I hear ya, mom." Dean makes his way up the stairs and sneezes again.

XXXXX

Dean groans as he wakes up, the sun rudely blinding him through his window. His head is pounding and he can't stop coughing to save his life. He groggily gets up out of bed and makes his way downstairs fighting off a massive coughing fit, but it wins out.

Sam looks up at him and grimaces. "Dean, you're sick, go back to bed."

"I'm fine," Dean argues.

"You're not fine. I heard you dying all the way up in your room. Now go to bed before you get worse."

"Sammy, I said I'm fi-" he gets cut off by another series of coughs and Sam glares at him in his I-told-you-so kind of way.

"I'll call Cas."

Dean glares at Sam. "Don't yo-" Dean, yet again, gets interrupted by a series of nasty sounding coughs.

Sam goes to say something about it but is cut off by his phone starting to sing to them. He digs it out of his pocket and sees Gabriel calling so he answers it, leaving the kitchen so he can hear Gabriel over Dean's coughing. "Hello?"

"Samerella, you …" Gabriel goes silent on the other end of the line for a few seconds before speaking up again. "You good over there?"

He must have heard Dean in the background. "Oh, yeah, I'm fine." Sam walks back into the kitchen to see Dean nursing a glass of water at the table. "Dean is just sick and being stubborn saying he's fine. Did you need something?"

"Ah, no, I was calling to see if you and Dean-o wanted to go out and have a little fun tonight, but that cough sounds pretty nasty. Wasn't he and Cassie out on a date yesterday?"

"Yeah, that's how he got sick."

"Well, the offer still stands for you if you want to get out of the house."

"No, I should stay here. Dean's a pain in the ass when he's sick because he thinks he's fine _when he's clearly not_." Sam emphasizes that last part for Dean, in which case Dean simply rolls his eyes at his brother. "Thanks for the offer though, Gabriel."

"Anytime, good luck on your end of things."

Soon after they hang up, Sam finally kicks Dean up the steps to his room. When Dean is in bed he tells him, "Stay, sleep." and it makes him feel like he's talking to an unruly dog. Dean stays up in his room for at least an hour before making his way back down the stairs, earning an annoyed, "Dean," from his brother in the living room. In which Dean responded with a petulant, "I can't sleep, Sammy, let me do something, I'm going mad here."

A knock on the door stops Sam momentarily from commanding his brother upstairs again, but as he gets up he looks at him and says, "Go to bed, Dean. I'll bring something to help you sleep." and then he opens the door. His eyes widen seeing Cas standing there with a white pot of, what looks like, chicken noodle soup.

"Cas, what're you doing here?"

Cas gives a sheepish smile holding out the pot for Sam to take, which he does. "I made chicken noodle soup for you both. I feel like it's partially my fault Dean got sick from being in the rain yesterday."

"How'd you …" Sam pauses and nods, no longer needing to ask. "Gabriel told you?"

"Yes," Cas nods pulling out his phone and showing Sam the text.

 **Gabriel:** Little bro, you got your boyfriend sick yesterday and now he's giving Sam grey hairs, go save the moose from greying early.

Sam rolls his eyes. "Don't listen to him, Cas, it wasn't your fault. You can come in."

Sam steps aside and Cas thanks him coming in just as Dean starts having another coughing fit in the kitchen. Sam and Cas make their way into the kitchen, Sam setting the soup on the stove.

Dean straightens up from supporting himself on the counter and looks back to see what the noise was Sam made, but instead, he makes eye contact. A small smile makes its way onto Dean's face. "Cas, when did-" He quickly turns his head and coughs a few more times in his elbow, the quick movement makes him stumble a bit but Cas steadies him. "When'd you get here?"

"A minute ago. Gabriel informed me you got sick so I made you some soup."

"You didn't have to do that, Cas." Dean hesitates to look over at the stove, nibbling at his bottom lip. "Is it chicken noodle?"

Cas can't help but smile seeing his appetite hasn't been affected. "Yes, it is. And if you go to bed you can have some."

Dean's smile falls and he huffs petulantly and starts making his way upstairs mumbling something about him coming into his house and ordering him around, but he goes anyway. Cas smiles and watches him disappear up the steps before looking over to Sam. Sam looks impressed that Cas got Dean to go to his room on the first try, but then again, it was for food; food that Cas made specifically for him.

"I have to say I'm surprised," Cas says while Sam goes and gets a bowl for Dean. "He got awfully sick in one night."

"Yeah, I know, but that's how it is with Dean. It's always been like that. He rarely gets sick, but when he does it hits him like a train. Hard, fast, and all at once." Sam sighs turning to face him. "And even when he's this sick, he will keep going until he passes out, claiming he's fine."

Cas offers out a hand for the bowl. "I can take that to him."

Sam hands it over along with a bottle of pills and a bottle of water. "Thanks, Cas."

Cas smiles and brings everything upstairs and to Dean's room. Dean is sitting in bed with his back against the wall and his eyes closed, he doesn't open them until he hears Cas putting the bowl down on the nightstand by his bed. He looks over and Cas hold out a hand that has pills in them.

"It's fine, Cas, I don't need them."

"Dean, don't make me force feed you."

Dean whistles and smirks at him. "Seeing you get all demanding is making me tingly, Cas." Dean's smirk is wiped from his face when he goes into another coughing fit, successfully making Cas roll his eyes. "Really, Cas," Dean starts, cringing at a pain in his chest. "I don't need them."

"Why not?"

"I don't want them."

Cas narrows his eyes. "You're worse than a petulant child."

Dean goes to grab the soup bowl but Cas swats his hand away. Dean looks up at him surprised and slightly confused. "You said I could have it if I went to my room."

"And now I'm saying you can have it after you take the medicine."

Dean eventually relents and begrudgingly takes the stupid medicine. Cas finally lets Dean eat the soup, which Dean says tastes amazing and tells Cas he's a great cook. After Dean is finished eating, Cas takes the bowl and tells Dean to get some sleep, adding a little please to the end so Dean will be more inclined to listen. When Cas gets downstairs he rinses the bowl and puts it in the dishwasher.

"Is he actually sleeping now?" Sam asks coming into the kitchen.

"I hope so," Cas says turning to Sam. "Did Dean happen to clean out his car last night?"

Sam furrows his brows. "No, why? What's in it?"

"Mud." Cas reminds him and Sam's mouth forms into an o shape remembering Dean came home looking like he crawled out of a swamp, and that's how they find themselves out by Dean's car cleaning her out for him.

Cas' phone starts to ring in his pocket and he backs out of the car looking at the screen. Cas sighs and Sam straightens out as well looking at him. Cas meets his eyes. "I'm sorry, I really should take this."

"Yeah, go ahead."

Cas turns away and walks a little down the driveway answering the call. "Yes, Michael?"

"I just read something that said you were dating some man, Castiel, who is he?"

Cas runs a hand down his face slightly annoyed, but knowing Michael is his brother and of course he would want to know who his little brother is dating. "It isn't anybody you know, he's Gabriel's friend."

The other end of the line is silent for a moment. "Of course it would be Gabriel," Michael sighs. "Castiel, I don't think you have time for such things as a relationship right now. You're very busy with the show. It's close to the finale, can't this little … thing wait until after?"

"Michael, I have plenty of time for this."

"If you say so, but Castiel, you know Gabriel's friends aren't always the best. What if this man is simply using y-"

Cas hangs up on him, not trusting himself to keep calm if he were to answer Michael. He will deal with him later, but right now he's with Sam and he doesn't want to cause a scene. Cas takes a deep breath and goes to pocket his phone, but it starts to ring again, so Cas turns it on airplane mode before cramming it back in his pocket. He makes his way back to Sam and begins to clean again.

Sam looks up and sees Cas is clearly upset by something. "You okay?"

Cas looks up at him with a smile. "Yes, I'm fine. It was just my brother."

"Gabriel?"

"Michael."

And with that, they keep quiet and clean the rest of the car. The two of them have a few good laughs about what happened yesterday and when it comes time for Cas to leave, he makes his way to tell Dean he's heading out, but Dean is asleep on his bed. Cas smiles and walks over quietly, leaning down and placing a gentle kiss on his forehead whispering, "Goodbye, Dean." before leaving.


End file.
